Ketone or oxime compound, and herbicide

ABSTRACT

There is provided novel agricultural chemicals, in particular herbicides. A ketone or oxime compound or a salt thereof of Formula (1): 
     
       
         
         
             
             
         
       
     
     wherein B is a ring of any one of B-1, B-2, or B-3, Q is an oxygen atom, a sulfur atom, NOR 7 , etc., R 6  is a hydrogen atom, C 1-6  alkyl, etc., R 7  is a hydrogen atom, C 1-6  alkyl, etc., R 8a , R 8b , R 9a , R 9b , R 10 , R 11 , R 12 , R 13 , and R 14  are each independently a hydrogen atom, C 1-6  alkyl, etc., m is an integer of 1 or 2, n is an integer of 0, 1 or 2; and a herbicide including the compound or salt thereof.

TECHNICAL FIELD

The present invention relates to a novel ketone or oxime compound or a salt thereof, and agricultural chemicals, in particular herbicides, containing the ketone or oxime compound or the salt thereof as an active component. The agricultural chemical in the present invention means an insecticide/acaricide, a nematicide, a herbicide, and a bactericide in agricultural and horticultural fields.

BACKGROUND ART

For example, certain types of ketone or oxime compounds have been described in Patent Documents 1 to 4. The ketone or the oxime compound according to the present invention, however, has not been described at all.

PRIOR ART DOCUMENTS Patent Documents

-   Patent Document 1: WO2001/017972 Pamphlet -   Patent Document 2: WO2003/062244 Pamphlet -   Patent Document 3: WO2010/000773 Pamphlet -   Patent Document 4: WO2010/069834 Pamphlet

SUMMARY OF THE INVENTION Problem to be Solved by the Invention

An object of the present invention is to provide a chemical substance that surely shows effect on various weeds in a low application amount of the chemical substance, has reduced land pollution and reduced influence on succeeding crops, and high safety, and is useful as an active component of herbicides.

Means for Solving the Problem

As a result of intensive investigation for solving the problem, the inventors of the present invention have found that a novel ketone or oxime compound of Formula (1) below according to the present invention has excellent herbicidal activity as a herbicide and high safety against target crops as well as has almost no adverse effect on non-target creatures such as mammals, fish, and beneficial insects, and is an extremely useful compound, and thus have accomplished the present invention.

More specifically, the present invention relates to the following [1] to [151].

A ketone or oxime compound or a salt thereof of Formula (1):

[wherein B is a ring of any one of B-1, B-2, or B-3;

Q is an oxygen atom, a sulfur atom, or NOR⁷;

A is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁵, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, —S(O)_(r2)R¹, —C(O)OR¹, —C(S)OR¹, —C(O)SR¹, —C(S)SR¹, —C(O)R², —C(S)R², —C(O)N(R⁴)R³, —C(S)N(R⁴)R³, —S(O)₂N(R⁴)R³, —P(O)(OR¹)₂, or —P(S)(OR¹)₂;

R¹ is C₁₋₈ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, phenyl, or phenyl substituted with (Z²)_(q2);

R² is a hydrogen atom, C₁₋₈ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, —C(═NOR³¹)R³², phenyl, phenyl substituted with (Z²)_(q2), naphthyl, naphthyl substituted with (Z²)_(q2), D1-1 to D1-42, D1-81, or D1-84;

R³ and R⁴ are each independently a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, phenyl, phenyl substituted with (Z²)_(q2), D1-32, D1-33 or D1-34, or R³ optionally forms a 3- to 8-membered ring together with a nitrogen atom to which R³ and R⁴ are bonded by forming a C₂₋₇ alkylene chain or a C₂₋₇ alkenylene chain together with R⁴, and at this time, the alkylene chain or the alkenylene chain optionally contains one oxygen atom, sulfur atom, or nitrogen atom and optionally substituted with C₁₋₆ alkyl, oxo, or thioxo;

R⁵ is a halogen atom, cyano, nitro, C₃₋₈ cycloalkyl, —OR³¹, —S(O)_(r2)R³¹, —C(O)OR³¹, —C(O)R³², —N(R³⁴)R³³, —Si(R^(32a))(R^(32b))R^(32c), phenyl, phenyl substituted with (Z²)_(q2), D1-1, D1-32, D1-33, or D1-34, or when two R⁵s are substituents on a same carbon, the two R⁵s optionally form oxo, thioxo, imino, C₁₋₆ alkylimino, C₁₋₆ alkoxyimino, or C₁₋₆ alkylidene, together with each other,

R⁶ is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R¹⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R¹⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R¹⁵, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R¹⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R¹⁵, —C(═NOR¹⁶)R¹⁷, phenyl, phenyl substituted with (Z¹)_(q1), D1-32, D1-33, D1-34, D1-36, D1-37, or D1-38;

R⁷ is a hydrogen atom, C₁₋₈ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R^(15b), C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R^(15b), C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R^(15b), C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R^(15b), C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R^(15b), phenyl, or phenyl substituted with (Z¹)_(q1);

R^(8a), R^(8b), R^(9a), and R^(9b) are each independently a hydrogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, —OR^(16a), —S(O)_(r1)R^(16a), —C(O)OR^(16a), —C(O)R^(17a), —C(O)N(R^(19a))R^(18a), —C(═NOR^(16a))R^(17a), phenyl, or phenyl substituted with (Z¹)_(q1);

R¹⁰, R¹¹ and R¹² are each independently a hydrogen atom or C₁₋₆ alkyl;

R¹⁵ is a halogen atom, cyano, C₃₋₈ cycloalkyl, —OR¹⁶, —S(O)_(r1)R¹⁶, phenyl, phenyl substituted with (Z¹)_(q1), D1-7, D1-11, D1-22, D1-32, D1-33, or D1-34;

R^(15b) is a halogen atom, cyano, C₃₋₈ cycloalkyl, halo (C₃₋₈) cycloalkyl, —OR^(16b), —S(O)_(r1)R^(16b), —C(O)OR^(16b), —C(O)N(R^(18b))R^(19b), —C(═NOR^(16b))R^(17b), —N(R^(18b))R^(19b), —Si(R^(32a))(R^(32b))R^(32c), phenyl, phenyl substituted with (Z¹)_(q1), D1-32, D1-33, D1-34, D1-36, D1-37, D1-38, D1-81, or D1-84, or when two R^(15b)s are substituents on a same carbon, the two R^(15b)s optionally form oxo, thioxo, imino, C₁₋₆ alkylimino, C₁₋₆ alkoxyimino, or C₁₋₆ alkylidene, together with each other;

R¹⁶, R^(16a), R^(16b), R¹⁷, R^(17a), R^(17b), R^(18a), and R^(19a) are each independently a hydrogen atom or C₁₋₆ alkyl;

R^(18b) and R^(19b) are each independently a hydrogen atom, C₁₋₆ alkyl, or (C₁₋₆) alkyl arbitrarily substituted with R²⁰, or R^(18b) optionally forms a 3- to 8-membered ring together with a nitrogen atom to which R^(18b) and R^(19b) are bonded by forming a C₂₋₇ alkylene chain or a C₂₋₇ alkenylene chain together with R^(19b), and at this time, the alkylene chain or the alkenylene chain optionally contains one oxygen atom, sulfur atom, or nitrogen atom and optionally substituted with oxo or thioxo;

R²⁰ is phenyl or phenyl substituted with (Z¹)_(q1);

D1-1 to D1-42, D1-81, and D1-84 each are a ring of the following structure;

X¹ is a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, or C₃₋₈ cycloalkyl, when g2, g3, or g4 is an integer of 2 or larger, each X¹ is the same as or different from each other, and further when two X¹s are adjacent, the two adjacent X¹s optionally form a 6-membered ring together with carbon atoms to which each X¹ is bonded by forming —CH═CHCH═CH—, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is optionally substituted with a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, or C₁₋₆ alkylsulfonyl;

X^(1a) is a hydrogen atom or C₁₋₆ alkyl;

X^(1b) is C₁₋₆ alkyl;

Z is a halogen atom, cyano, nitro, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁴⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁴⁵, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁴⁵, —OR⁴¹, —S(O)_(r3)R⁴¹, —C(O)OR⁴¹, —C(O)R⁴², —C(═NOR⁴¹)R⁴², —N(R⁴⁴)R⁴³, phenyl, phenyl substituted with (Z³)_(q3), D1-1, D1-2, D1-7, D1-10, D1-11, D1-22, D1-32, D1-33, D1-34, D1-36, D1-37, or D1-38, and when q is an integer of 2 or larger, each Z¹ is the same as or different from each other;

Z¹ is a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, or C₁₋₆ alkoxycarbonyl, and when q1 is an integer of 2 or larger, each Z¹ is the same as or different from each other;

Z² is a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, —OR⁵¹, —S(O)_(r2)R⁵¹, —C(O)OR^(51a), —C(O)R⁵², —C(O)N(R⁵⁴)R⁵³, —C(S)N(R⁵⁴)R⁵³, or —N(R⁵⁴)R⁵³, when q2 is an integer of 2 or larger, each Z² is the same as or different from each other, and further when two Z²s are adjacent, the two adjacent Z²s optionally form a 6-membered ring together with carbon atoms to which each Z² is bonded by forming —N═CHCH═CH—, —CH═NCH═CH—, —N═NCH═CH—, —CH═NN═CH—, —N═CHCH═N—, or —N═CHN═CH—, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is optionally substituted with a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, or C₁₋₆ alkylsulfonyl;

Z³ is a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, halo (C₁₋₆) alkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, or C₁₋₆ alkylsulfonyl, and when q3 is an integer of 2 or larger, each Z³ is the same as or different from each other,

R³¹ is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R³⁵, —C(O)R³⁷, phenyl, phenyl substituted with (Z²)_(q2), naphthyl, or naphthyl substituted with (Z²)_(q2);

R³² is a hydrogen atom, C₁₋₆ alkyl, or (C₁₋₆) alkyl arbitrarily substituted with R³⁵;

R^(32a), R^(32b), and R^(32c) are each independently C₁₋₆ alkyl;

R³³ and R³⁴ are each independently a hydrogen atom, C₁₋₆ alkyl, —C(O)OR³⁶, or —C(O)R³⁷;

R³⁵ is a halogen atom, C₁₋₆ alkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or phenyl;

R³⁶ is C₁₋₆ alkyl;

R³⁷ is a hydrogen atom, C₁₋₆ alkyl, phenyl, or phenyl substituted with (Z²)_(q2);

R⁴¹ is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁴⁵, phenyl, phenyl substituted with (Z³)_(q3), D1-32, D1-33, or D1-34;

R⁴² is a hydrogen atom or C₁₋₆ alkyl;

R⁴³ and R⁴⁴ are each independently a hydrogen atom, C₁₋₆ alkyl, C₁₋₆ alkoxycarbonyl, or C₁₋₆ alkylcarbonyl;

R⁴⁵ is a halogen atom, C₃₋₈ cycloalkyl, —OH, C₁₋₆ alkoxy, C₁₋₁₀ alkoxycarbonyl, —Si(R^(32a))(R^(32b))R^(32c), phenyl, phenyl substituted with (Z³)_(q3), D1-32, D1-33, or D1-34, or when two R⁴⁵s are substituents on a same carbon, the two R⁴⁵s optionally form oxo, thioxo, imino, C₁₋₆ alkylimino, C₁₋₆ alkoxyimino, or C₁₋₆ alkylidene, together with each other;

R⁵¹ is a hydrogen atom, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, phenyl, phenyl arbitrarily substituted with a halogen atom, or D1-39;

R^(51a) and R⁵² are each independently a hydrogen atom or C₁₋₆ alkyl;

R⁵³ and R⁵⁴ are each independently a hydrogen atom, C₁₋₆ alkyl, or C₁₋₆ alkylcarbonyl;

f5 is an integer of 0, 1, 2, 3, 4, or 5;

f7 is an integer of 0, 1, 2, 3, 4, 5, 6, or 7;

g1 and p are each independently an integer of 0 or 1;

g2, m, n, r1, r2, and r3 are each independently an integer of 0, 1, or 2;

g3 is an integer of 0, 1, 2, or 3;

g4 is an integer of 0, 1, 2, 3, or 4; and

q, q1, q2, and q3 are each independently an integer of 1, 2, 3, 4, or 5].

[2]

The ketone or oxime compound or a salt thereof according to [1], in which B is a ring of either B-1-a or B-2-a; and

Z^(a), Z^(c) and Z^(e) are each independently a hydrogen atom, a halogen atom, cyano, nitro, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁴⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁴⁵, —OR⁴¹, —S(O)_(r3)R⁴¹, —C(O)OR⁴¹, —C(O)R⁴², —C(═NOR⁴¹)R⁴², —N(R⁴⁴)R⁴³, phenyl, phenyl substituted with (Z³)_(q3), D1-1, D1-2, D1-7, D1-10, D1-11, D1-22, D1-32, D1-33, D1-34, D1-36, D1-37, or D1-38.

[3]

The ketone compound or the salt thereof according to [2], in which Q is an oxygen atom.

[4]

The oxime compound or a salt thereof according to [2], in which Q is ═NOR⁷.

[5]

The ketone compound or the salt thereof according to [3], in which A is a hydrogen atom, C₁₋₆ alkyl, or —C(O)R²;

R² is C₁₋₈ alkyl;

R⁶ is C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R¹⁵, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, —C(═NOR¹⁶)R¹⁷, phenyl, phenyl substituted with (Z¹)_(q1), or D1-32;

R^(8a) is a hydrogen atom, C₁₋₆ alkyl, —C(O)OR^(16a), or —C(O)R^(17a);

R^(9a) is a hydrogen atom or C₁₋₆ alkyl;

R^(8b) and R^(9b) are hydrogen atoms;

R¹⁰, R¹¹, and R¹² are hydrogen atoms;

R¹⁵ is a halogen atom, C₃₋₈ cycloalkyl, —OR¹⁶, or phenyl;

R¹⁶, R^(16a), R¹⁷, and R^(17a) are each independently C₁₋₆ alkyl;

X¹ is halo (C₁₋₆) alkyl;

Z^(a), Z^(c) and Z^(e) are each independently a hydrogen atom, a halogen atom, C₁₋₆ alkyl, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkynyl, —OR⁴¹, phenyl, phenyl substituted with (Z³)_(q3), D1-7, D1-11, D1-22, D1-32, or D1-37;

Z¹ is a halogen atom;

Z³ is a halogen atom, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, halo (C₁₋₆) alkoxy, or C₁₋₆ alkylthio;

R⁴¹ is C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁴⁵, phenyl, D1-32, or D1-34;

R⁴⁵ is a halogen atom, phenyl, or D1-34;

g2, g3, and p are 0;

q1 and q3 are integers of 1; and

g4, m, and n are each independently an integer of 0 or 1.

[6]

The ketone compound or the salt thereof according to [5], in which B is B-1-a;

Z^(a) is a halogen atom, C₁₋₆ alkyl, or C₁₋₆ alkoxy;

Z^(c) is a halogen atom, C₁₋₆ alkyl, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁴⁵, C₂₋₄ alkynyl, —OR⁴¹, phenyl, phenyl substituted with (Z³)_(q3), D1-7, D1-1, D1-22, D1-32, or D1-37; and

Z^(e) is a halogen atom or C₁₋₆ alkyl.

[7]

The oxime compound or the salt thereof according to [4], in which A is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, —S(O)_(r2)R¹, —C(O)OR¹, —C(O)SR¹, —C(S)OR¹, —C(O)R², —C(O)N(R⁴)R³, —C(S)N(R⁴)R³, or —S(O)₂N(R⁴)R³;

R¹ is C₁₋₈ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, phenyl, or phenyl substituted with (Z²)_(q2);

R² is C₁₋₈ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, —C(═NOR³¹)R³², phenyl, phenyl substituted with (Z²)_(q2), D1-5, D1-6, D1-8, D1-10, or D1-81;

R³ is C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, phenyl, or phenyl substituted with (Z²)_(q2), or R³ forms a 5- to 6-membered ring together with a nitrogen atom to which R³ and R⁴ are bonded by forming a C₄ or C₅ alkylene chain together with R⁴, and at this time, the alkylene chain optionally contains one oxygen atom or nitrogen atom and is optionally substituted with C₁₋₄ alkyl;

R⁴ is C₁₋₆ alkyl, C₂₋₆ alkenyl, or phenyl;

R⁵ is a halogen atom, cyano, C₃₋₈ cycloalkyl, —OR³¹, —S(O)_(r2)R³¹, —C(O)OR³¹, —C(O)R³², —N(R³⁴)R³³, —Si(R^(32a))(R^(32b))R^(32c), phenyl, phenyl substituted with (Z²)_(q2), or D1-1, or when two R⁵s are substituents on a same carbon, the two R⁵s optionally form C₁₋₆ alkoxyimino together with each other;

R⁶ is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R¹⁵, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, —C(═NOR¹⁶)R¹⁷, phenyl, phenyl substituted with (Z¹)_(q1) or, D1-32;

R⁷ is a hydrogen atom, C₁₋₇ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R^(15b), C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, C₃₋₈ cycloalkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R^(15b), C₂₋₆ alkynyl, or phenyl;

R^(8a) is a hydrogen atom, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, —C(O)OR^(16a), —C(═NOR^(16a))R^(17a), or phenyl substituted with (Z¹)_(q1);

R^(9a) is a hydrogen atom or C₁₋₆ alkyl;

R^(8b) and R^(9b) are hydrogen atoms;

R¹² is a hydrogen atom;

R¹⁵ is a halogen atom, C₃₋₈ cycloalkyl, or —OR¹⁶;

R^(15b) is a halogen atom, cyano, C₃₋₈ cycloalkyl, halo (C₃₋₈) cycloalkyl, —OR^(16b), —S(O)_(r1)R^(16b), —C(O)OR^(16b), —C(O)N(R^(18b))R^(19b), —C(═NOR^(16b))R^(17b), —N(R^(18b))R^(19b), —Si(R^(32a))(R^(32b))R^(32c), phenyl, phenyl substituted with (Z¹)_(q1), D1-32, or D1-84;

R¹⁶, R^(16a), R¹⁷, R^(17a), and R^(17b) are each independently C₁₋₆ alkyl;

R^(18b) is a hydrogen atom, C₁₋₆ alkyl, or (C₁₋₆) alkyl arbitrarily substituted with R²⁰, or R^(18b) forms a 6-membered ring together with a nitrogen atom to which R^(18b) and R^(19b) are bonded by forming a C₅ alkylene chain together with R^(19b), and at this time, the alkylene chain contains one oxygen atom;

R^(19b) is a hydrogen atom or C₁₋₆ alkyl;

R²⁰ is phenyl substituted with (Z¹)_(q1);

X¹ is a halogen atom, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, or C₃₋₈ cycloalkyl, g3 is an integer of 2, and further the two adjacent X¹s form a 6-membered ring together with carbon atoms to which each X¹ is bonded by forming —CH═CHCH═CH—, and at this time, one hydrogen atom bonded to each carbon atom forming the ring is arbitrarily substituted with a halogen atom;

X^(1a) is C₁₋₆ alkyl;

Z^(a), Z^(c), and Z^(e) are each independently a hydrogen atom, a halogen atom, cyano, nitro, C₁₋₆ alkyl, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁴⁵, —OR⁴¹, —S(O)_(r3)R⁴¹, —C(O)OR⁴¹, —C(O)R⁴², —C(═NOR⁴¹)R⁴², —N(R⁴⁴)R⁴³, phenyl, phenyl substituted with (Z³)_(q3), D1-2, D1-7, D1-1, D1-22, D1-32, D1-33, D1-34, or D1-37,

Z¹ is a halogen atom, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, or C₁₋₆ alkoxycarbonyl, and when q1 is an integer of 2 or larger, each Z¹ is the same as or different from each other;

Z² is a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, —OR⁵¹, —S(O)_(r2)R⁵¹, —C(O)OR^(51a), —C(O)R⁵², or —C(O)N(R⁵⁴)R⁵³, when q2 is an integer of 2 or larger, each Z² is the same as or different from each other, and further when the two Z²s are adjacent, the two adjacent Z²s optionally form a 6-membered ring together with carbon atoms to which each Z² is bonded by forming —N═CHCH═CH—, and at this time, one hydrogen atom bonded to each carbon atom forming the ring is arbitrarily substituted with a halogen atom;

Z³ is a halogen atom, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, halo (C₁₋₆) alkoxy, or C₁₋₆ alkylthio, and when q3 is an integer of 2 or larger, each Z³ is the same as or different from each other;

R³¹ is C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R³⁵, —C(O)R³⁷, phenyl, phenyl substituted with (Z²)_(q2), or naphthyl;

R³² is C₁₋₆ alkyl or (C₁₋₆) alkyl arbitrarily substituted with R³⁵;

R³³ is —C(O)R³⁷;

R³⁴ is C₁₋₆ alkyl;

R³⁵ is a halogen atom, C₁₋₆ alkylthio, or phenyl;

R³⁷ is C₁₋₆ alkyl or phenyl;

R⁴¹ is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁴⁵, phenyl, or D1-32;

R⁴² is C₁₋₆ alkyl;

R⁴³ is C₁₋₆ alkoxycarbonyl;

R⁴⁴ is a hydrogen atom;

R⁴⁵ is a halogen atom, C₃₋₈ cycloalkyl, —OH, C₁₋₆ alkoxy, C₁₋₁₀ alkoxycarbonyl, —Si(R^(32a))(R^(32b))R^(32c), phenyl, or D1-34;

R⁵¹ is C₁₋₆ alkyl, halo (C₁₋₆) alkyl, phenyl arbitrarily substituted with a halogen atom, or D1-39;

R^(51a) is C₁₋₆ alkyl;

R⁵³ and R⁵⁴ are each independently C₁₋₆ alkyl;

g2 is an integer of 0, 1, or 2;

g3 and r1 are each independently an integer of 0, 1, or 2;

g4, m, and n are each independently an integer of 0 or 1;

f7, p, and r3 are 0;

q is an integer of 2 or 3;

q1 is an integer of 1 or 2;

q2 is an integer of 1, 2, or 3;

q3 is an integer of 1, 2, or 3; and

r2 is an integer of 0 or 2.

[8]

The oxime compound or the salt according to [7], in which B is B-1-a;

Z^(a) is a halogen atom, C₁₋₆ alkyl, C₁₋₆ alkoxy, or C₁₋₆ alkylthio;

Z^(c) is a hydrogen atom, a halogen atom, cyano, nitro, C₁₋₆ alkyl, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁴⁵, —OR⁴¹, —S(O)₃R⁴¹, —C(O)OR⁴¹, —C(O)R⁴², —C(═NOR⁴¹)R⁴², —N(R⁴⁴)R⁴³, phenyl, phenyl substituted with (Z³)_(q3), D1-2, D1-7, D1-11, D1-22, D1-32, D1-33, D1-34, or D1-37;

Z^(e) is a halogen atom, C₁₋₆ alkyl, or C₁₋₆ alkoxy;

X¹ is a halogen atom or halo (C₁₋₆) alkyl; and

g3 is an integer of 0 or 1.

[9]

The ketone or oxime compound or the salt thereof according to [1], in which B is B-1 or B-2.

[10]

The ketone or oxime compound or the salt thereof according to [1], in which B is B-1.

[11]

The ketone or oxime compound or the salt thereof according to [1], in which B is B-2.

[12]

The ketone or oxime compound or the salt thereof according to [1], in which B is B-3.

[13]

The ketone or oxime compound or the salt thereof according to [2], in which B is B-1-a.

[14]

The ketone or oxime compound or the salt thereof according to [2], in which B is B-1-b.

[15]

The ketone compound or the salt thereof according to [3], in which B is B-1 or B-2.

[16]

The ketone compound or the salt thereof according to [3], in which B is B-1.

[17]

The ketone compound or the salt thereof according to [3], in which B is B-2.

[18]

The ketone compound or the salt thereof according to [3], in which B is B-3.

[19]

The ketone compound or the salt thereof according to [3] and [5], in which B is B-1-a.

[20]

The ketone compound or the salt thereof according to [3] and [5], in which B is B-1-b.

[21]

The oxime compound or the salt thereof according to [4], in which B is B-1 or B-2.

[22]

The oxime compound or the salt thereof according to [4], in which B is B-1.

[23]

The oxime compound or the salt thereof according to [4], in which B is B-2.

[24]

The oxime compound or the salt thereof according to [4], in which B is B-3.

[25]

The oxime compound or the salt thereof according to [4] and [7], in which B is B-1-a.

[26]

The oxime compound or the salt thereof according to [4] and [7], in which B is B-1-b.

[27]

The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, or (C₂₋₆) alkynyl arbitrarily substituted with R⁵.

[28]

The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, C₂₋₆ alkynyl, or (C₂₋₆) alkynyl arbitrarily substituted with R⁵.

[29]

The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is a hydrogen atom, C₁₋₆ alkyl, or (C₁₋₆) alkyl arbitrarily substituted with R⁵.

[30]

The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is a hydrogen atom, —S(O)_(r2)R¹, —C(O)OR¹, —C(O)SR¹, —C(S)OR¹, —C(O)R², —C(O)N(R⁴)R³, —C(S)N(R⁴)R³, or —S(O)₂N(R⁴)R³.

[31]

The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is a hydrogen atom, —C(O)OR¹, —C(O)SR¹, —C(O)R², —C(O)N(R⁴)R³, or —C(S)N(R⁴)R³.

[32]

The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is a hydrogen atom, —C(O)SR¹, —C(O)R², or —C(O)N(R⁴)R³.

[33]

The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is a hydrogen atom.

[34]

The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is C₁₋₆ alkyl or (C₁₋₆) alkyl arbitrarily substituted with R⁵.

[35]

The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is C₂₋₆ alkynyl or (C₂₋₆) alkynyl arbitrarily substituted with R⁵.

[36]

The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is —C(O)SR¹.

[37]

The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is a —C(O)R².

[38]

The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is —C(O)N(R⁴)R³.

[39]

The ketone or oxime compound or the salt thereof according to [1] to [26], in which A is —C(S)N(R⁴)R³.

[40]

The ketone or oxime compound or the salt thereof according to [1] to [39], in which R¹ is C₁₋₈ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, or C₂₋₆ alkenyl.

[41]

The ketone or oxime compound or the salt thereof according to [1] to [39], in which R¹ is C₁₋₈ alkyl.

[42]

The ketone or oxime compound or the salt thereof according to [1] to [39], in which R¹ is (C₁₋₆) alkyl arbitrarily substituted with R⁵.

[43]

The ketone or oxime compound or the salt thereof according to [1] to [39], in which R¹ is C₃₋₈ cycloalkyl.

[44]

The ketone or oxime compound or the salt thereof according to [1] to [39], in which R¹ is C₂₋₆ alkenyl.

[45]

The ketone or oxime compound or the salt thereof according to [1] to [44], in which R² is C₁₋₈ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, or —C(═NOR³¹)R³².

[46]

The ketone or oxime compound or the salt thereof according to [1] to [44], in which R² is C₁₋₈ alkyl or (C₁₋₆) alkyl arbitrarily substituted with R⁵.

[47]

The ketone or oxime compound or the salt thereof according to [1] to [44], in which R² is C₃₋₈ cycloalkyl or (C₃₋₈) cycloalkyl arbitrarily substituted with R⁵.

[48]

The ketone or oxime compound or the salt thereof according to [1] to [44], in which R² is C₂₋₆ alkenyl or (C₂₋₆) alkenyl arbitrarily substituted with R⁵.

[49]

The ketone or oxime compound or the salt thereof according to [1] to [44], in which R² is C₃₋₈ cycloalkenyl or (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁵.

[50]

The ketone or oxime compound or the salt thereof according to [1] to [44], in which R² is C₂₋₆ alkynyl or (C₂₋₆) alkynyl arbitrarily substituted with R⁵.

[51]

The ketone or oxime compound or the salt thereof according to [1] to [44], in which R² is phenyl, phenyl substituted with (Z²)_(q2), D1-5, D1-6, D1-8, D1-10, or D1-81.

[52]

The ketone or oxime compound or the salt thereof according to [1] to [44], in which R² is C₁₋₈ alkyl.

[53]

The ketone or oxime compound or the salt thereof according to [1] to [44], in which R² is (C₁₋₆) alkyl arbitrarily substituted with R⁵.

[54]

The ketone or oxime compound or the salt thereof according to [1] to [53], in which R³ is C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, phenyl, or phenyl substituted with (Z²)_(q2).

[55]

The ketone or oxime compound or the salt thereof according to [1] to [53], in which R³ is C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, or C₂₋₆ alkenyl.

[56]

The ketone or oxime compound or the salt thereof according to [1] to [53], in which R³ is phenyl or phenyl substituted with (Z²)_(q2).

[57]

The ketone or oxime compound or the salt thereof according to [I] to [53], in which R³ forms a 5- or 6-membered ring together with a nitrogen atom to which R³ and R¹ are bonded by forming a C₄ or C₅ alkylene chain together with R⁴, and at this time, the alkylene chain optionally contains one oxygen atom or nitrogen atom and is optionally substituted with C₁₋₆ alkyl.

[58]

The ketone or oxime compound or the salt thereof according to [1] to [57], in which R⁵ is a halogen atom, cyano, C₃₋₈ cycloalkyl, —OR³¹, —S(O)_(r2)R³¹, —C(O)OR³¹, phenyl, or phenyl substituted with (Z²)_(q2).

[59]

The ketone or oxime compound or the salt thereof according to [1] to [57], in which R⁵ is a halogen atom, —OR³, or —S(O)_(r2)R³¹.

[60]

The ketone or oxime compound or the salt thereof according to [1] to [57], in which R⁵ is a halogen atom.

[61]

The ketone or oxime compound or the salt thereof according to [1] to [57], in which R⁵ is —OR³¹.

[62]

The ketone or oxime compound or the salt thereof according to [1] to [57], in which R⁵ is —S(O)_(r2)R³¹.

[63]

The ketone or oxime compound or the salt thereof according to [1] to [57], in which, when two R⁵s are substituents on a same carbon, the two R⁵s optionally form C₁₋₆ alkoxyimino together with each other.

[64]

The ketone or oxime compound or the salt thereof according to [1] to [63], in which R⁶ is C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R¹⁵, C₃₋₈ cycloalkyl, or C₂₋₆ alkenyl.

[65]

The ketone or oxime compound or the salt thereof according to [1] to [63], in which R⁶ is phenyl, phenyl substituted with (Z¹)_(q1), or D1-32.

[66]

The ketone or oxime compound or the salt thereof according to [1] to [63], in which R⁶ is C₁₋₆ alkyl or C₃₋₈ cycloalkyl.

[67]

The ketone or oxime compound or the salt thereof according to [1] to [63], in which R⁶ is C₁₋₆ alkyl.

[68]

The ketone or oxime compound or the salt thereof according to [1] to [63], in which R⁶ is C₃₋₈ cycloalkyl.

[69]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [63], in which R⁷ is a hydrogen atom, C₁₋₇ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R^(15b), C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, C₃₋₈ cycloalkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R^(15b), or C₂₋₆ alkynyl.

[70]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [63], in which R⁷ is a hydrogen atom, C₁₋₇ alkyl, or (C₁₋₆) alkyl arbitrarily substituted with R^(15b).

[71]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [63], in which R⁷ is a hydrogen atom.

[72]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [63], in which R⁷ is C₁₋₇ alkyl.

[73]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [63], in which R⁷ is (C₁₋₆) alkyl arbitrarily substituted with R^(15b).

[74]

The ketone or oxime compound or the salt thereof according to [1] to [73], in which R⁵ is a hydrogen atom, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, or —C(O)OR¹⁶.

[75]

The ketone or oxime compound or the salt thereof according to [1] to [73], in which R^(8a) is a hydrogen atom or C₁₋₆ alkyl.

[76]

The ketone or oxime compound or the salt thereof according to [1] to [73], in which R^(8a) is a hydrogen atom.

[77]

The ketone or oxime compound or the salt thereof according to [1] to [73], in which R^(5a) is C₁₋₆ alkyl.

[78]

The ketone or oxime compound or the salt thereof according to [1] to [77], in which R^(9a) is a hydrogen atom.

[79]

The ketone or oxime compound or the salt thereof according to [1] to [79], in which R^(9a) is C₁₋₆ alkyl.

[80]

The ketone or oxime compound or the salt thereof according to [1] to [79], in which R¹⁵ is a halogen atom.

[81]

The ketone or oxime compound or the salt thereof according to [1] to [79], in which R¹⁵ is C₃₋₈ cycloalkyl.

[82]

The ketone or oxime compound or the salt thereof according to [1] to [79], in which R¹⁵ is —OR¹⁶.

[83]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [82], in which R^(15b) is a halogen atom, cyano, halo (C₃₋₈) cycloalkyl, —OR^(16b), —S(O)_(r1)R^(16b), or —C(O)N(R^(18b))R^(19b).

[84]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [82], in which R^(15b) is a halogen atom, cyano, —OR^(16b), or —S(O)_(r1)R^(16b).

[85]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [82], in which R^(15b) is a halogen atom.

[86]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [82], in which R^(15b) is cyano.

[87]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [82], in which R^(15b) is —OR^(16b).

[88]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [82], in which R^(15b) is —S(O)_(r1)R^(16b).

[89]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [82], in which R^(15b) is phenyl, phenyl substituted with (Z¹)_(q1), D1-32, or D1-84.

[90]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [82], in which R^(15b) is phenyl or phenyl substituted with (Z¹)_(q1).

[91]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [90], in which R^(18b) is a hydrogen atom or C₁₋₆ alkyl.

[92]

The oxime compound or the salt thereof according to [1], [2], [4], [7] to [14], and [21] to [90], in which R^(18b) forms a 6-membered ring together with a nitrogen atom to which R^(18b) and R^(19b) are bonded by forming a C₅ alkylene chain together with R^(19b), and at this time, the alkylene chain contains one oxygen atom.

[93]

The ketone or oxime compound or the salt thereof according to [1] to [92], in which X¹ is halo (C₁₋₆) alkyl or C₃₋₈ cycloalkyl.

[94]

The ketone or oxime compound or the salt thereof according to [1] to [92], in which X¹ is a halogen atom or C₁₋₆ alkyl.

[95]

The ketone or oxime compound or the salt thereof according to [1] to [92], in which X¹ is a halogen atom.

[96]

The ketone or oxime compound or the salt thereof according to [1] to [92], in which X¹ is C₁₋₆ alkyl.

[97]

The ketone or oxime compound or the salt thereof according to [1] to [96], in which Z^(a) is a halogen atom.

[98]

The ketone or oxime compound or the salt thereof according to [1] to [96], in which Z^(a) is C₁₋₆ alkyl.

[99]

The ketone or oxime compound or the salt thereof according to [1] to [96], in which Z^(a) is C₁₋₆ alkoxy.

[100]

The ketone or oxime compound or the salt thereof according to [1] to [96], in which Z^(a) is C₁₋₆ alkylthio.

[101]

The ketone or oxime compound or the salt thereof according to [1] to [100], in which Z^(c) is a hydrogen atom, a halogen atom, cyano, C₁₋₆ alkyl, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁴⁵, phenyl, phenyl substituted with (Z³)_(q3), D1-2, D1-7, D1-11, D1-22, D1-32, D1-33, D1-34, or D1-37.

[102]

The ketone or oxime compound or the salt thereof according to [1] to [100], in which Z^(c) is a hydrogen atom, a halogen atom, cyano, C₁₋₆ alkyl, C₂₋₆ alkynyl, or (C₂₋₆) alkynyl arbitrarily substituted with R⁴⁵.

[103]

The ketone or oxime compound or the salt thereof according to [1] to [100], in which Z^(c) is phenyl, phenyl substituted with (Z³)_(q3), D1-2, D1-7, D1-11, D1-22, D1-32, D1-33, D1-34, or D1-37.

[104]

The ketone or oxime compound or the salt thereof according to [1] to [100], in which Z^(c) is C₁₋₆ alkyl.

[105]

The ketone or oxime compound or the salt thereof according to [1] to [100], in which Z^(c) is C₂₋₆ alkynyl or (C₂₋₆) alkynyl arbitrarily substituted with R⁴⁵.

[106]

The ketone or oxime compound or the salt thereof according to [1] to [100], in which Z^(c) is phenyl or phenyl substituted with (Z³)_(q3).

[107]

The ketone or oxime compound or the salt thereof according to [1] to [100], in which Z^(c) is D1-2, D1-7, D1-32, D1-33, D1-34, or D1-37.

[108]

The ketone or oxime compound or the salt thereof according to [1] to [100], in which Z^(c) is D1-32, D1-33, or D1-34.

[109]

The ketone or oxime compound or the salt thereof according to [1] to [100], in which Z^(c) is D1-7.

[110]

The ketone or oxime compound or the salt thereof according to [1] to [109], in which Z^(e) is a halogen atom.

[111]

The ketone or oxime compound or the salt thereof according to [1] to [109], in which Z^(e) is C₁₋₆ alkyl.

[112]

The ketone or oxime compound or the salt thereof according to [1] to [109], in which Z^(e) is C₁₋₆ alkoxy.

[113]

The ketone or oxime compound or the salt thereof according to [1] to [109], in which Z^(e) is C₁₋₆ alkylthio.

[114]

The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z² is a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, —OR⁵¹, or —S(O)_(r2)R⁵¹.

[115]

The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z² is a halogen atom, cyano, nitro, C₁₋₆ alkyl, or halo (C₁₋₆) alkyl.

[116]

The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z² is a halogen atom or C₁₋₆ alkyl.

[117]

The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z² is —OR⁵¹ or —S(O)_(r2)R⁵¹.

[118]

The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z² is a halogen atom.

[119]

The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z² is C₁₋₆ alkyl.

[120]

The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z² is —OR⁵¹.

[121]

The ketone or oxime compound or the salt thereof according to [1] to [113], in which Z² is —S(O)_(r2)R⁵¹.

[122]

The ketone or oxime compound or the salt thereof according to [1] to [121], in which Z³ is a halogen atom or halo (C₁₋₆) alkoxy.

[123]

The ketone or oxime compound or the salt thereof according to [1] to [121], in which Z³ is a halogen atom.

[124]

The ketone or oxime compound or the salt thereof according to [1] to [121], in which Z³ is halo (C₁₋₆) alkoxy.

[125]

The ketone or oxime compound or the salt thereof according to [1] to [124], in which R³² is C₁₋₆ alkyl.

[126]

The ketone or oxime compound or the salt thereof according to [1] to [124], in which R³² is (C₁₋₆) alkyl arbitrarily substituted with R³⁵.

[127]

The ketone or oxime compound or the salt thereof according to [1] to [126], in which R³⁵ is a halogen atom.

[128]

The ketone or oxime compound or the salt thereof according to [1] to [126], in which R^(3s) is C₁₋₆ alkylthio.

[129]

The ketone or oxime compound or the salt thereof according to [1] to [126], in which R³⁵ is phenyl.

[0130]

The ketone or oxime compound or the salt thereof according to [1] to [129], in which R³⁷ is C₁₋₆ alkyl.

[131]

The ketone or oxime compound or the salt thereof according to [1] to [129], in which R³⁷ is phenyl.

[132]

The ketone or oxime compound or the salt thereof according to [1] to [131], in which R⁴¹ is a hydrogen atom, C₁₋₆ alkyl, or (C₁₋₆) alkyl arbitrarily substituted with R⁴⁵.

[133]

The ketone or oxime compound or the salt thereof according to [1] to [131], in which R⁴¹ is phenyl or D1-32.

[134]

The ketone or oxime compound or the salt thereof according to [1] to [131], in which R⁴¹ is a hydrogen atom.

[135]

The ketone or oxime compound or the salt thereof according to [1] to [131], in which R⁴¹ is C₁₋₆ alkyl.

[136]

The ketone or oxime compound or the salt thereof according to [1] to [131], in which R⁴¹ is (C₁₋₆) alkyl arbitrarily substituted with R⁴⁵.

[137]

The ketone or oxime compound or the salt thereof according to [1] to [136], in which R⁴⁵ is a halogen atom, C₃₋₈ cycloalkyl, —OH, or C₁₋₆ alkoxy.

[138]

The ketone or oxime compound or the salt thereof according to [1] to [136], in which R⁴⁵ is phenyl or D1-34.

[139]

The ketone or oxime compound or the salt thereof according to [1] to [136], in which R⁴⁵ is a halogen atom.

[140]

The ketone or oxime compound or the salt thereof according to [1] to [136], in which R⁴⁵ is C₃₋₈ cycloalkyl.

[141]

The ketone or oxime compound or the salt thereof according to [1] to [136], in which R⁴⁵ is —OH.

[142]

The ketone or oxime compound or the salt thereof according to [1] to [136], in which R⁴⁵ is C₁₋₆ alkoxy.

[143]

The ketone or oxime compound or the salt thereof according to [1] to [142], in which R⁵¹ is C₁₋₆ alkyl.

[144]

The ketone or oxime compound or the salt thereof according to [1] to [143], in which m is an integer of 0 or 1.

[145]

The ketone or oxime compound or the salt thereof according to [1] to [143], in which m is an integer of 0.

[146]

The ketone or oxime compound or the salt thereof according to [1] to [143], in which m is an integer of 1.

[147]

The ketone or oxime compound or the salt thereof according to [1] to [146], in which n is an integer of 0 or 1.

[148]

The ketone or oxime compound or the salt thereof according to [1] to [146], in which n is an integer of 0.

[149]

The ketone or oxime compound or the salt thereof according to [1] to [146], in which n is an integer of 1.

[150]

An agricultural chemical comprising one or more of compounds selected from the ketone or oxime compound or the salt thereof according to [1] to [149] as an active component.

[151]

A herbicide comprising one or more of compounds selected from the ketone or oxime compound or the salt thereof according to [1] to [149] as an active component.

Effects of the Invention

The compound of the present invention has excellent herbicidal activity against various weeds and has high safety to target crops as well as has almost no adverse effect on non-target creatures such as mammals, fish, and beneficial insects and has light environmental burden due to low residual properties.

Accordingly, the present invention can provide a useful herbicide in the agricultural and horticultural fields such as paddy fields, farmlands, and orchards.

MODES FOR CARRYING OUT THE INVENTION

The compound of Formula (1) of the present invention may exist as, for example, keto-enol structural tautomers of the following formula depending on the kind of the substituent and conditions. The present invention includes all of these structures.

The compounds included in the present invention may include the geometric isomers of an E-form having an E-configuration and a Z-form having a Z-configuration depending on the types of the substituents. The present invention includes the E-form, the Z-form, and a mixture of the E-form and the Z-form in any ratios. In the present specification, these forms are represented as, for example, a bond of wavy lines illustrated below.

The compounds included in the present invention include optically active isomers due to the existence of one or more of asymmetric carbon atoms. The present invention includes all optically active isomers or racemic forms.

Among the compounds included in the present invention, the compounds that can form an acid-added salt by a conventional method may form, for example, the salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydroiodic acid; the salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, and perchloric acid; the salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, and p-toluenesulfonic acid; the salts of carboxylic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, and citric acid; or the salts of amino acids such as glutamic acid and aspartic acid.

Among the compounds included in the present invention, the compounds that can form a metal salt by a conventional method may form, for example, the salts of alkali metals such as lithium, sodium, and potassium; the salts of alkaline earth metals such as calcium, barium, and magnesium; or the salt of aluminum.

Subsequently, specific examples of each substituent described in the present specification will be described below. Here, n—means normal; i—means iso; s—means secondary; and tert—means tertiary; and Ph means phenyl.

Examples of the halogen atom in the present specification may include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. The expression of “halo” in the present specification is also these halogen atoms.

The expression of C_(a-b) alkyl in the present specification is a linear chain or a branched chain hydrocarbon group made of the number of carbon atoms of a to b. Specific examples of the C_(a-b) alkyl may include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group, and n-hexyl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of C_(a-b) alkenyl in the present specification is a linear chain or a branched chain unsaturated hydrocarbon group made of the number of carbon atoms of a to b and having one or more double bonds in the molecule. Specific examples of the C_(a-b) alkenyl may include vinyl group, 1-propenyl group, 2-propenyl group, 1-methylethenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, and 1,1-dimethyl-2-propenyl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of C_(a-b) alkynyl in the present specification is a linear chain or a branched chain unsaturated hydrocarbon group made of the number of carbon atoms of a to b and having one or more triple bonds in the molecule. Specific examples of the C_(a-b) alkenyl may include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, and 1,1-dimethyl-2-propynyl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of halo (C_(a-b)) alkyl in the present specification is a linear chain or a branched chain hydrocarbon group made of the number of carbon atoms of a to b in which the hydrogen atoms bonded to the carbon atom are arbitrarily substituted with halogen atoms. When the compound is substituted with two or more halogen atoms, these halogen atoms may be the same as or different from each other. Specific examples of the C_(a-b) haloalkyl may include fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2,2-trichloroethyl group, 1,1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, and nonafluorobutyl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of C_(a-b) cycloalkyl in the present specification is a cyclic hydrocarbon group made of the number of carbon atoms of a to b and can form a monocyclic structure or a fused ring structure of a 3-membered ring to a 6-membered ring. Each ring is optionally substituted with an alkyl group in a range of the specified number of carbon atoms. Specific example of the C_(a-b) cycloalkyl may include cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of halo (C_(a-b)) cycloalkyl in the present specification is a cyclic hydrocarbon group made of the number of carbon atoms of a to b in which the hydrogen atoms bonded to the carbon atom are arbitrarily substituted with halogen atoms and can form a monocyclic structure or a conjugated-cyclic structure of a 3-membered ring to a 6-membered ring. Each ring can be optionally substituted with an alkyl group in a range of the specified number of carbon atoms. The substitution position with the halogen atom may be at a ring structure part, at a side chain structure part, or at both of them. When the compound is substituted with two or more halogen atoms, these halogen atoms may be the same as or different from each other. Specific examples of the halo (C_(a-b)) cycloalkyl may include 2,2-difluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, 2,2-difluoro-1-methylcyclopropyl group, 2,2-dichloro-1-methylcyclopropyl group, 2,2-dibromo-1-methylcyclopropyl group, and 2,2,3,3-tetrafluorocyclobutyl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of C_(a-b) cycloalkenyl in the present specification is a cyclic unsaturated hydrocarbon group made of the number of carbon atoms of a to b and having one or more double bonds and can form a monocyclic structure or a fused ring structure of a 3-membered ring to a 6-membered ring. Each ring can be optionally substituted with an alkyl group in a range of the specified number of carbon atoms. The double bond may be either an endo-form or an exo-form. Specific example of the C_(a-b) cycloalkenyl may include 1-cyclopentene-1-yl group, 2-cyclopentene-1-yl group, 1-cyclohexen-1-yl group, and 2-cyclohexen-1-yl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of C_(a-b) alkoxy in the present specification is an alkyl-O— group in which this alkyl is the above meaning alkyl made of the number of carbon atoms of a to b. Specific examples of the C_(a-b) alkoxy may include methoxy group, ethoxy group, n-propyloxy group, i-propyloxy group, n-butyloxy group, i-butyloxy group, s-butyloxy group, and tert-butyloxy group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of halo (C_(a-b)) alkoxy in the present specification is a haloalkyl-O— group in which this haloalkyl is the above meaning haloalkyl made of the number of carbon atoms of a to b. Specific examples of the halo (C_(a-b)) alkoxy may include difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, 2-chloro-1,1,2-trifluoroethoxy group, and 1,1,2,3,3,3-hexafluoropropyloxy group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of C_(a-b) alkylthio in the present specification is an alkyl-S— group in which this alkyl is the above meaning alkyl made of the number of carbon atoms of a to b. Specific examples of the C_(a-b) alkylthio may include methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, and tert-butylthio group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of C_(a-b) alkylsulfinyl in the present specification is an alkyl-S(O)— group in which this alkyl is the above meaning alkyl made of the number of carbon atoms of a to b. Specific examples of the C_(a-b) alkylsulfinyl may include methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, s-butylsulfinyl group, and tert-butylsulfinyl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of C_(a-b) alkylsulfonyl in the present specification is an alkyl-SO₂— group in which this alkyl is the above meaning alkyl made of the number of carbon atoms of a to b. Specific examples of the C_(a-b) alkylsulfonyl may include methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, s-butylsulfonyl group, and tert-butylsulfonyl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of C_(a-b) alkoxycarbonyl in the present specification is an alkyl-O—C(O)— group in which this alkyl is the above meaning alkyl made of the number of carbon atoms of a to b. Specific examples of the C_(a-b) alkoxycarbonyl may include methoxycarbonyl group, ethoxycarbonyl group, n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, and tert-butoxycarbonyl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of C_(a-b) alkylcarbonyl in the present specification is an alkyl-C(O)— group in which this alkyl is the above meaning alkyl made of the number of carbon atoms of a to b. Specific examples of the C_(a-b) alkylcarbonyl may include acetyl group, propionyl group, butyryl group, isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, hexanoyl group, and heptanoyl group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of C_(a-b) alkylimino in the present specification is an alkyl-N=group in which this alkyl is the above meaning alkyl made of the number of carbon atoms of a to b. Specific examples of the C_(a-b) alkylimino may include methylimino group, ethylimino group, n-propylimino group, i-propylimino group, n-butylimino group, i-butylimino group, and s-butylimino group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of C_(a-b) alkoxyimino in the present specification is an alkoxy-N=group in which this alkoxy is the above meaning alkoxy made of the number of carbon atoms of a to b. Specific examples of the C_(a-b) alkoxyimino may include methoxyimino group, ethoxyimino group, n-propyloxyimino group, i-propyloxyimino group, and n-butyloxyimino group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of C_(a-b) alkylidene in the present specification is a linear or branched hydrocarbon group made of the number of carbon atoms of a to b and bonded with a double bond. Specific examples of the C_(a-b) alkylidene may include methylidene group, ethylidene group, propylidene group, and 1-methylethylidene group and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

The expression of “(C_(a-b)) alkyl arbitrarily substituted with R⁵”, “(C_(a-b)) alkyl arbitrarily substituted with R¹⁵”, “(C_(a-b)) alkyl arbitrarily substituted with R^(15b)”, “(C_(a-b)) alkyl arbitrarily substituted with R²⁰”, “(C_(a-b)) alkyl arbitrarily substituted with R³⁵”, or “(C_(a-b)) alkyl arbitrarily substituted with R⁴⁵” in the present specification is the above meaning alkyl group made of the carbon number of a to b in which the hydrogen atoms bonded to the carbon atoms are arbitrarily substituted with any R⁵, R¹⁵, R^(15b), R²⁰, R³⁵, or R⁴⁵. Each of these groups is selected in a range of the specified number of carbon atoms. At this time, when two or more substituents R⁵s, R¹⁵s, R^(15b)s, R²⁰s, R³⁵s, or R⁴⁵s are contained in each (C_(a-b)) alkyl group, each R⁵, R¹⁵, R^(15b), R²⁰, R³⁵, or R⁴⁵ may be the same as or different from each other.

The expression of “(C_(a-b)) cycloalkyl arbitrarily substituted with R⁵”, “(C_(a-b)) cycloalkyl arbitrarily substituted with R¹⁵”, “(C_(a-b)) cycloalkyl arbitrarily substituted with R^(15b)”, or “(C_(a-b)) cycloalkyl arbitrarily substituted with R⁴⁵” in the present specification is the above meaning cycloalkyl group made of the carbon number of a to b in which the hydrogen atoms bonded to the carbon atoms are arbitrarily substituted with any R⁵, R¹⁵, R^(15b), or R⁴⁵. Each of these groups is selected in a range of the specified number of carbon atoms. At this time, when two or more substituents R⁵s, R¹⁵s, R^(15b)s, or R⁴⁵s are contained in each (C_(a-b)) cycloalkyl group, each R⁵, R¹⁵, R^(15b), or R⁴⁵ may be the same as or different from each other. The substituted positions may be at a ring structure part, at a side chain structure part, or at both of them.

The expression of “(C_(a-b)) alkenyl arbitrarily substituted with R⁵”, “(C_(a-b)) alkenyl arbitrarily substituted with R¹⁵”, “(C_(a-b)) alkenyl arbitrarily substituted with R^(15b)”, or “(C_(a-b)) alkenyl arbitrarily substituted with R⁴⁵” in the present specification is the above meaning alkenyl group made of the carbon number of a to b in which the hydrogen atoms bonded to the carbon atoms are arbitrarily substituted with any R⁵, R¹⁵, R^(15b), or R⁴⁵. Each of these groups is selected in a range of the specified number of carbon atoms. At this time, when two or more substituents R⁵s, R¹⁵s, R^(15b)s, or R⁴⁵s are contained in each (C_(a-b)) alkenyl group, each R⁵, R¹⁵, R^(15b), or R⁴⁵ may be the same as or different from each other.

The expression of “(C_(a-b)) cycloalkenyl arbitrarily substituted with R⁵”, “(C_(a-b)) cycloalkenyl arbitrarily substituted with R¹⁵”, “(C_(a-b)) cycloalkenyl arbitrarily substituted with R^(15b)”, or “(C_(b)) cycloalkenyl arbitrarily substituted with R⁴⁵” in the present specification is the above meaning cycloalkenyl group made of the carbon number of a to b in which the hydrogen atoms bonded to the carbon atoms are arbitrarily substituted with any R⁵, R¹⁵, R^(15b), or R⁴⁵. Each of these groups is selected in a range of the specified number of carbon atoms. At this time, when two or more substituents R⁵s, R¹⁵s, R^(15b)s, or R⁴⁵s are contained in each (C_(a-b)) cycloalkenyl group, each R⁵, R¹⁵, R^(15b), or R⁴⁵ may be the same as or different from each other. The substituted positions may be at a ring structure part, at a side chain structure part, or at both of them.

The expression of “(C_(a-b)) alkynyl arbitrarily substituted with R⁵”, “(C_(a-b)) alkynyl arbitrarily substituted with R¹⁵”, “(C_(a-b)) alkynyl arbitrarily substituted with R^(15b)”, or “(C_(a-b)) alkynyl arbitrarily substituted with R⁴⁵” in the present specification is the above meaning alkynyl group made of the carbon number of a to b in which the hydrogen atoms bonded to the carbon atoms are arbitrarily substituted with any R⁵, R¹⁵, R^(15b), or R⁴⁵. Each of these groups is selected in a range of the specified number of carbon atoms. At this time, when two or more substituents R⁵s, R¹⁵s, R^(15b)s, or R⁴⁵s are contained in each (C_(a-b)) alkynyl group, each R⁵, R¹⁵, R^(15b), or R⁴⁵ may be the same as or different from each other.

Specific examples of the expression of “R³ optionally forms a 3-membered ring to an 8-membered ring together with a nitrogen atom to which R³ and R⁴ are bonded by forming a C₂₋₇ alkylene chain or a C₂₋₇ alkenylene chain together with R⁴, and at this time, the alkylene chain or the alkenylene chain optionally contain one oxygen atom, one sulfur atom, or one nitrogen atom” include aziridine, azetidine, azetidin-2-one, pyrrolidine, pyrrolidin-2-one, oxazolidine, oxazolidin-2-one, oxazolidine-2-thione, thiazolidine, thiazolidin-2-one, thiazolidine-2-thione, imidazolidine, imidazolidin-2-one, imidazolidine-2-thione, piperidine, piperidin-2-one, piperidine-2-thione, 2H-3,4,5,6-tetrahydro-1,3-oxazin-2-one, 2H-3,4,5,6-tetrahydro-1,3-oxazine-2-thione, morpholine, 2H-3,4,5,6-tetrahydro-1,3-thiazin-2-one, 2H-3,4,5,6-tetrahydro-1,3-thiazine-2-thione, thiomorpholine, perhydropyrimidine-2-one, piperazine, homopiperidine, homopiperidin-2-one, heptamethyleneimine, 1,2-dihydropyridine, 1,2-dihydropyrimidine, 1,4-dihydropyridine, 2,3-dihydro-1H-imidazole, 2,3-dihydrothiazole, 2,3-dihydrooxazole, 4,5-dihydro-1H-pyrazole, 2,5-dihydro-1H-pyrrole, 1,2,3,4-tetrahydropyridine, 1,2,3,4-tetrahydropyrimidine, and 1,2,3,4-tetrahydropyridazine and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

Specific examples of the expression of “R^(18b) optionally forms a 3-membered ring to an 8-membered ring together with a nitrogen atom to which R^(18b) and R^(19b) are bonded by forming a C₂₋₇ alkylene chain together with R^(19b), and at this time, the alkylene chain contain one oxygen atom, one sulfur atom, or one nitrogen atom” include aziridine, azetidine, azetidin-2-one, pyrrolidin, pyrrolidin-2-one, oxazolidine, oxazolidin-2-one, oxazolidine-2-thione, thiazolidine, thiazolidin-2-one, thiazolidine-2-thione, imidazolidine, imidazolidin-2-one, imidazolidine-2-thione, piperidine, piperidin-2-one, piperidine-2-thione, 2H-3,4,5,6-tetrahydro-1,3-oxazin-2-one, 2H-3,4,5,6-tetrahydro-1,3-oxazine-2-thione, morpholine, 2H-3,4,5,6-tetrahydro-1,3-thiazin-2-one, 2H-3,4,5,6-tetrahydro-1,3-thiazine-2-thione, thiomorpholine, perhydropyrimidin-2-one, piperazine, homopiperidine, homopiperidin-2-one, and heptamethyleneimine and the like. Each of these groups is selected in a range of the specified number of carbon atoms.

Subsequently, the production method of the compound of the present invention will be described below. In Production Method A to Production Method K, A¹ in formulas is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁵, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, —S(O)_(r2)R¹, —C(O)OR¹, —C(S)OR¹, —C(O)SR¹, —C(S)SR¹, —C(O)R², —C(S)R², —C(O)N(R⁴)R³, —C(S)N(R⁴)R³, —S(O)₂N(R⁴)R³, —P(O)(OR¹)₂, or —P(S)(OR¹)₂ and R¹, R⁵, R², R³, R⁴ and r2 have the same meanings as defined above.

Production Method A

In the compounds of the present invention, the compound of Formula (1-1) of the present invention [wherein Q, A¹, R⁶, R^(8a), R^(8b), R^(9a), R^(9b), Z, m, n, and q have the same meanings as defined above.] and the compound of Formula (1-2) of the present invention [Q, A¹, R⁶, R^(8a), R^(8b), R^(9a), R^(9b), Z, m, n, and q have the same meanings as defined above.] can be produced by reacting the compound of Formula (1-1-a) with a compound of Formula (7-1) [wherein J^(a) is a leaving group such as a halogen atom, —OSO₂Me, and —OSO₂CF₃ and A¹ has the same meaning as defined above.].

Some of the compounds of Formula (7-1) are known compounds and some of the compounds are commercially available. The compounds other than the known compounds or the commercially available compounds can be synthesized in accordance with methods described in documents.

In this reaction, the compound of Formula (7-1) can be used in a range of 0.5 equivalent to 50 equivalents relative to 1 equivalent of the compound of Formula (1-1-a). Bases such as triethylamine, pyridine, 4-(dimethylamino)pyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, n-butyllithium, lithium diisopropylamide, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, sodium hydride, sodium methoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate can be used, if necessary.

This reaction may be carried out in the absence of a solvent or may be carried out using a solvent. Examples of the solvent may include polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone; alcohols such as methanol, ethanol, propanol, 2-propanol, and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether, aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.

As the reaction temperature, any temperature from −80° C. to the reflux temperature of the reaction mixture can be set. The reaction time varies depending on the concentration of the reactant and the reaction temperature, and usually the time may be set in a range of 5 minutes to 100 hours.

Production Method B

In the compounds of Formula (1-1-a), the compound of Formula (1-1-a2) of the present invention [wherein R⁶, R⁷, R^(8a), R^(8b), R^(9a), R^(9b), Z, m, n, and q have the same meanings as defined above.] can be produced by reacting the compound of Formula (1-1-a1) [wherein R⁶, R^(8a), R^(8b), R^(9a), R^(9b), Z, m, n, and q have the same meanings as defined above.] with a compound of Formula (3) [wherein R⁷ has the same meaning as defined above.].

Some of the compounds of Formula (3) are known compounds and some of the compounds are commercially available. The compounds other than the known compounds or the commercially available compounds can be synthesized in accordance with methods described in documents.

In this reaction, the compound of Formula (3) can be used in a range of 0.1 equivalent to 100 equivalent relative to 1 equivalent of the compound of Formula (1-1-a1). Bases such as potassium carbonate, triethylamine, pyridine, and 4-(dimethylamino)pyridine can be used, if necessary.

This reaction may be carried out in the absence of a solvent or may be carried out using a solvent. Examples of the solvent may include polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone; alcohols such as methanol, ethanol, propanol, 2-propanol, and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.

As the reaction temperature, any temperature from −80° C. to the reflux temperature of the reaction mixture can be set. The reaction time varies depending on the concentration of the reactant and the reaction temperature, and usually the time may be set in a range of 5 minutes to 100 hours.

Production Method C

In the compounds of Formula (1-1), the compound of Formula (1-1-a1) of the present invention can be obtained by hydrolyzing the compound of Formula (1-1-b) [wherein R⁶, R⁷, R^(8a), R^(8b), R^(9a), R^(9b), Z, m, n, and q have the same meanings as defined above, A³ is C₁₋₆ alkyl or (C₁₋₆) alkyl arbitrarily substituted with R⁵, and R⁵ has the same meaning as defined above.].

In this reaction, solvents such as water, methanol, ethanol, dichloromethane, chloroform, diethyl ether, tetrahydrofuran, 1,4-dioxane, acetonitrile, and acetone may be used, if necessary. These solvents may be used singly or in combination of two or more of them.

The reaction can be carried out in the presence of 0.1 equivalent to 20 equivalents of an acid such as hydrochloric acid, sulfuric acid, or p-toluenesulfonic acid relative to 1 equivalent of the compound of Formula (1-1-b), if necessary.

As the reaction temperature, any temperature from −80° C. to the reflux temperature of the reaction mixture can be set. The reaction time varies depending on the concentration of the reactant and the reaction temperature, and usually the time may be set in a range of 5 minutes to 100 hours.

Production Method D

In the compounds of Formula (1-1), the compound of Formula (1-1-b) of the present invention [wherein R⁶, R⁷, R^(8a), R^(8b), R⁹, R^(9b), Z, m, n and q have the same meanings as defined above, A³ is C₁₋₆ alkyl or (C₁₋₆) alkyl arbitrarily substituted with R⁵, and R⁵ has the same meaning as defined above.] can be produced by reacting the compound of Formula (4) [wherein Z and q have the same meanings as defined above, A³ is C₁₋₆ alkyl or (C₁₋₆) alkyl arbitrarily substituted with R⁵, and R⁵ has the same meaning as defined above.] with the compound of Formula (5) [wherein J^(a), R⁶, R⁷, R^(8a), R^(8b), R^(9a), R^(9b), m, and n have the same meanings as defined above.].

Some of the compounds of Formula (4) are known compounds. The compounds other than the known compounds can be produced in accordance with the known methods described in, for example, Chemische Berichte, 1983, Vol. 116, P. 119.

Some of the compounds of Formula (5) are known compounds. The compounds other than the known compounds can be produced in accordance with the known methods described in, for example, Synthesis, 1982, P. 305.

In this reaction, the compound of Formula (5) can be used in a range of 0.5 equivalent to 50 equivalents relative to 1 equivalent of the compound of Formula (4). Bases such as n-butyllithium, lithium diisopropylamide, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, sodium hydride, sodium methoxide, and potassium carbonate can be used, if necessary. This reaction may be carried out in the absence of a solvent or may be carried out using a solvent. Examples of the solvent may include polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 1-methyl-2-pyrrolidone, and 1,3-dimethyl-2-imidazolinone; alcohols such as methanol, ethanol, propanol, 2-propanol, and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether, and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.

As the reaction temperature, any temperature from −80° C. to the reflux temperature of the reaction mixture can be set. The reaction time varies depending on the concentration of the reactant and the reaction temperature, and usually the time may be set in a range of 5 minutes to 100 hours.

Production Method E

The compound of Formula (1-1-a3) of the present invention [wherein R⁶, R^(8a), R^(9a), Q, Z, and q have the same meanings as defined above.] can be produced by reacting the compound of Formula (9) [wherein Z and q have the same meanings as defined above.] with the compound of Formula (10) [wherein R⁶, R^(8a), R^(9a), and Q have the same meanings as defined above.].

Some of the compounds of Formula (9) are known compounds. The compounds other than the known compounds can be produced in accordance with the known methods described in, for example, WO 2009/019005 Pamphlet.

Some of the compounds of Formula (10) are known compounds and some of the compounds are commercially available. The compounds other than the known compound or the commercially available compounds can be synthesized in accordance with methods described in documents.

In this reaction, the compound of Formula (10) can be used in a range of 0.5 equivalent to 50 equivalents relative to 1 equivalent of the compound of Formula (9). Bases such as triethylamine, pyridine, 4-(dimethylamino)pyridine, 1,8-diazabicyclo[5.4.0]-7-undecene, n-butyllithium, lithium diisopropylamide, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, sodium hydride, sodium methoxide, sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate can be used, if necessary.

This reaction may be carried out in the absence of a solvent or may be carried out using a solvent. Examples of the solvent may include polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone; alcohols such as methanol, ethanol, propanol, 2-propanol, and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.

Production Method F

In the compounds of Formula (1-1-a), the compound of Formula (1-1-a5) of the present invention [wherein R⁶, R^(8a), Q, Z, and q have the same meanings as defined above.] can be obtained by hydrolyzing and then decarboxylating the compound of Formula (1-1-a4) [wherein R⁶, R^(8a), Q, Z, and q have the same meanings as defined above, R^(9a-2) is —C(O)OR^(16a), and R^(16a) has the same meaning as defined above.].

In this reaction, solvents such as water, methanol, ethanol, dichloromethane, chloroform, diethyl ether, tetrahydrofuran, 1,4-dioxane, acetonitrile, and acetone may be used, if necessary. These solvents may be used singly or in combination of two or more of them.

This reaction can be carried out in the presence of 0.1 equivalent to 20 equivalents of an acid such as hydrochloric acid, sulfuric acid, or p-toluenesulfonic acid or a base such as sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate relative to 1 equivalent of the compound of Formula (1-1-a4), if necessary.

As the reaction temperature, any temperature from −80° C. to the reflux temperature of the reaction mixture can be set. The reaction time varies depending on the concentration of the reactant and the reaction temperature, and usually the time may be set in a range of 5 minutes to 100 hours.

Production Method G

In the compounds of Formula (1-1-a), the compound of Formula (1-1-a7) of the present invention [wherein R⁶, R⁷, R^(8a), R^(8b), R^(9a), R^(9b), Z^(a), Z^(e), m, and n have the same meanings as defined above and Z^(c-2) has the same meaning as defined below.] can be produced by reacting the compound of Formula (1-1-a6) [wherein R⁶, R⁷, R^(8a), R^(8b), R^(9a), R^(9b), Z^(a), Z^(e), m, and n have the same meanings as defined above, and J^(b) is a leaving group such as a halogen atom, —OSO₂Me, —OSO₂CF₃.] with the compound of Formula (11) [wherein Z^(c-2) is C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁴⁵, phenyl, and phenyl substituted with (Z³)_(q3), J^(c) is —C(O)OH, —Sn(C₁₋₆ alkyl)₃, —B(OH)₂, and the like, and R⁴⁵, Z³ and q3 have the same meanings as described above.] in the presence of a catalyst and a base.

The amount of the compound of Formula (11) can be used in a range of 0.5 equivalent to 50 equivalents relative to 1 equivalent of the compound of Formula (1-1-a6).

Some of the compounds of Formula (11) used here are known compounds and some of the compounds are commercially available. The compounds other than the known compound or the commercially available compounds can be synthesized in accordance with methods described in documents.

Examples of the catalyst used in this reaction may include palladium catalysts such as palladium-carbon, palladium chloride, palladium acetate, bis(triphenylphosphine) palladium dichloride, tetrakis(triphenylphosphine) palladium, and [1,1′-bis(diphenylphosphino)ferrocene] palladium (II) dichloride dichloromethane adduct, and copper catalysts such as metal copper, copper acetate (monovalent), copper acetate (divalent), copper oxide (monovalent), copper oxide (divalent), copper iodide, copper bromide, and copper chloride. These catalysts can be used singly or in combination of two or more of them. The amount of the catalyst to be used can be used in a range of 0.001 equivalent to 1.0 equivalent relative to 1 equivalent of the compound of Formula (1-1-a6). Ligands such as 1,4-bis (diphenylphosphino)butane can be used in the range of 0.001 equivalent to 10 equivalents relative to the catalyst.

Examples of the base to be used may include tertiary amine compounds such as pyridine, diisopropylethylamine, and triethylamine and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, and tripotassium phosphate. The amount of the base to be used can be used in a range of 0.1 equivalent to 10.0 equivalents relative to 1 equivalent of the compound of Formula (11).

This reaction may be carried out in the absence of a solvent or may be carried out using a solvent. Example of usable solvents may include polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone, and water; alcohols such as methanol, ethanol, propanol, 2-propanol, and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether, aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.

As the reaction temperature, any temperature from −80° C. to the reflux temperature of the reaction mixture can be set. The reaction time varies depending on the concentration of the reactant and the reaction temperature, and usually the time may be set in a range of 5 minutes to 100 hours.

Production Method H

In the compounds of Formula (1-1-a), the compound of Formula (1-1-a8) of the present invention [wherein R⁶, R⁷, R^(8a), R^(8b), R^(9a), R^(9b), Z^(a), Z^(e), X¹, g3, m, and n have the same meanings as defined above.] can be produced by reacting the compound of Formula (1-1-a6) [wherein R⁶, R⁷, R^(8a), R^(8b), R^(9a), R^(9b), Z^(a), Z^(e), m, and n have the same meanings as defined above, and J^(b) is a leaving group such as a halogen atom, —OSO₂Me, —OSO₂CF₃.] with the compound of Formula (12) [wherein X¹ and g3 have the same meanings as defined above.] in the presence of a catalyst and a base.

The amount of the compound of Formula (12) can be used in a range of 0.5 equivalent to 50 equivalents relative to 1 equivalent of the compound of Formula (1-1-a6).

Some of the compounds of Formula (12) used here are known compounds and some of the compounds are commercially available. The compounds other than the known compound or the commercially available compounds can be synthesized in accordance with methods described in documents.

Examples of the catalyst used in this reaction may include palladium catalysts such as palladium-carbon, palladium chloride, palladium acetate, bis(triphenylphosphine) palladium dichloride, tetrakis(triphenylphosphine) palladium, and [1,1′-bis(diphenylphosphino)ferrocene] palladium (II) dichloride dichloromethane adduct, and copper catalysts such as metal copper, copper acetate (monovalent), copper acetate (divalent), copper oxide (monovalent), copper oxide (divalent), copper iodide, copper bromide, and copper chloride. These catalysts can be used singly or in combination of two or more of them. The amount of the catalyst to be used can be used in a range of 0.001 equivalent to 1.0 equivalent relative to 1 equivalent of the compound of Formula (1-1-a6). Ligands such as N,N′-dimethylethylenediamine and N,N′-dimethylcyclohexane-1,2-diamine can be used in the range of 0.001 equivalent to equivalents relative to the catalyst.

Examples of the base to be used may include tertiary amine compounds such as pyridine, diisopropylethylamine, and triethylamine and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, and tripotassium phosphate. The amount of the base to be used can be used in a range of 0.1 equivalent to 10.0 equivalents relative to 1 equivalent of the compound of Formula (12).

This reaction may be carried out in the absence of a solvent or may be carried out using a solvent. Example of usable solvents may include polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone, and water; alcohols such as methanol, ethanol, propanol, 2-propanol, and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.

As the reaction temperature, any temperature from −80° C. to the reflux temperature of the reaction mixture can be set. The reaction time varies depending on the concentration of the reactant and the reaction temperature, and usually the time may be set in a range of 5 minutes to 100 hours.

The reaction of Production Method A to Production Method H may be carried out under the atmosphere of inert gas such as nitrogen and argon, if necessary.

In Production Method A to Production Method H, usual post-treatment of the reaction mixture after completion of the reaction such as direct concentration, concentration after dissolving in an organic solvent and washing with water, or concentration after pouring in ice-water and extracting with an organic solvent can give the target compound of the present invention. When purification is required, the compound can be separated and purified by any purification method such as recrystallization and preparative isolation by column chromatography, thin layer chromatography, and liquid chromatography.

Production Method I

The compounds of Formula (1-3) of the present invention [wherein A¹, Q, R⁶, R^(8a), R^(8b), R^(9a), R^(9b), Z m, n, and q have the same meanings as defined above.] can be produced by reacting the mixture of the compound of Formula (13-1) [wherein R⁹⁰ is a leaving group such as C₁₋₆ alkoxy, pyrazol-1-yl, and imidazol-1-yl, and A¹, Q, R⁶, R^(8a), R^(8b), R^(9a), R^(9b), R⁹⁰, Z, m, n, and q have the same meanings as defined above.] and the compound of Formula (13-2) [wherein R⁹⁰ is a leaving group such as C₁₋₆ alkoxy, pyrazol-1-yl, and imidazol-1-yl, and A¹, Q, R⁶, R^(8a), R^(8b), R^(9a), R^(9b), R⁹⁰, Z, m, n, and q have the same meanings as defined above.] with a base.

Examples of the base to be used may include n-butyllithium, lithium diisopropylamide, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, sodium hydride, sodium methoxide, potassium carbonate, triethylamine, pyridine, 4-(dimethylamino)pyridine, and 1,8-diazabicyclo[5.4.0]-7-undecene. The amount of the base to be used can be used in a range of 0.1 equivalent to 10.0 equivalents relative to 1 equivalent of the mixture of the compound of Formula (13-1) and the compound of Formula (13-2).

This reaction may be carried out in the absence of a solvent or may be carried out using a solvent. Example of usable solvents may include polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, acetonitrile, dimethylsulfoxide, 1,3-dimethyl-2-imidazolinone, and water; alcohols such as methanol, ethanol, propanol, 2-propanol, and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether; aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as methylene chloride, chloroform, and carbon tetrachloride; and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.

As the reaction temperature, any temperature from −80° C. to the reflux temperature of the reaction mixture can be set. The reaction time varies depending on the concentration of the reactant and the reaction temperature, and usually the time may be set in a range of 5 minutes to 100 hours.

A mixture of the compound of Formula (13-1) and the compound of Formula (13-2) used in Production Method I can be produced in accordance with a production route described in Reaction Formula 1, for example.

Reaction Formula 1

Process 1

The mixture of the compound of Formula (17-1) [wherein A¹, Q, R⁶, R^(8a), R^(8b), R^(9a), R^(9b), Z, m, n, and q have the same meanings as defined above.] and the compound of Formula (17-2) [wherein A¹, Q, R⁶, R^(8a), R^(8b), R^(9a), R^(9b), Z, m, n, and q have the same meanings as defined above.] can be produced by reacting the compound of Formula (15) [wherein A¹, Z, and q have the same meanings as defined above.] with the compound of Formula (16) [wherein Q, R⁶, R^(8a), R^(8b), R^(9a), R^(9b), m, and n have the same meanings as defined above.] in accordance with known methods described in documents, for example, the method described in U. S. Patent No. 1981/4283348.

Some of the compounds of Formula (15) used here are known compounds and some of the compounds are commercially available. The compounds other than the known compounds or the commercially available compounds can be synthesized in accordance with methods described in documents.

Some of the compounds of Formula (16) are known compounds and can be produced in accordance with the known methods described in, for example, J. Chem. Soc., 1965, p. 4355.

Process 2

The mixture of the compound of Formula (13-1) and the compound of Formula (13-2) can be produced by reacting the mixture of the compound of Formula (17-1) and the compound of Formula (17-2) with a halogenating agent such as thionyl chloride or oxalyl chloride in accordance with known methods described in documents, for example, the method described in Jikken Kagaku Kouza 4th edition (The 4th edition of experimental chemistry) (edited by The Chemical Society of Japan) 1992, Vol. 22, P. 122, and thereafter reacting the resultant mixture with the compound of Formula (18) [wherein R⁹⁰ is C₁₋₆ alkoxy, pyrazol-1-yl, or imidazol-1-yl.] in accordance with known methods described in documents, for example, the method described in Jikken Kagaku Kouza 4th edition (The 4th edition of Experimental Chemistry) (edited by The Chemical Society of Japan) 1992, Vol. 22, P. 50.

Some of the compounds of Formula (18) used here are known compounds and some of the compounds are commercially available. The compounds other than the known compounds or the commercially available compounds can be synthesized in accordance with methods described in documents.

Production Method J

In the compounds of formula (1-1), the compound of Formula (1-1-b2) of the present invention [wherein A³, R⁶, R⁷, R^(8a), R^(8b), R^(9a), R^(9b), R¹⁰, Z, m, n, and q have the same meanings as defined above.] can be produced by reacting the compound of Formula (1-1-b) [wherein A³, R⁶, R⁷, R^(8a), R^(8b), R^(9a), R^(9b), Z, m, n, and q have the same meanings as defined above.] with the compound of Formula (19) [wherein R¹⁰ and J^(a) have the same meanings as defined above.].

Some of the compounds of Formula (19) are known compounds and some of the compounds are commercially available. The compounds other than the known compound or the commercially available compounds can be synthesized in accordance with methods described in documents.

In this reaction, the compound of Formula (19) can be used in a range of 0.5 equivalent to 50 equivalents relative to 1 equivalent of the compound of Formula (1-1-b). Bases such as n-butyllithium, lithium diisopropylamide, lithium bis(trimethylsilyl)amide, sodium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, sodium hydride, sodium methoxide, and potassium carbonate can be used in a range of 0.5 equivalent to 50.0 equivalents relative to 1 equivalent of the compound of Formula (1-1-b), if necessary.

This reaction may be carried out in the absence of a solvent or may be carried out using a solvent. Examples of the solvent may include polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 1-methyl-2-pyrrolidone, and 1,3-dimethyl-2-imidazolinone; alcohols such as methanol, ethanol, propanol, 2-propanol, and ethylene glycol; ethers such as diethyl ether, tetrahydrofuran, and diphenyl ether; and aliphatic hydrocarbons such as pentane and n-hexane. These solvents may be used singly or in combination of two or more of them.

As the reaction temperature, any temperature from −80° C. to the reflux temperature of the reaction mixture can be set. The reaction time varies depending on the concentration of the reactant and the reaction temperature, and usually the time may be set in a range of 5 minutes to 100 hours.

Production Method K

In the compounds of Formula (1-2), the compound of Formula (1-2-b2) of the present invention [wherein A³, R⁶, R⁷, R^(8a), R^(8b), R^(9a), R^(9b), R¹¹, Z, m, n, and q have the same meanings as defined above.] can be produced by reacting the compound of Formula (1-2-b) [wherein A³, R⁶, R⁷, R^(8a), R^(8b), R^(9a), R^(9b), Z, m, n, and q have the same meanings as defined above.] with the compound of Formula (20) [wherein R¹¹ and J^(a) have the same meanings as defined above.] in a similar method to Production Method J.

The compound of Formula (1-1-b) used in Production Method J and the compound of Formula (1-2-b) used in Production Method K can be produced as a mixture by Production Method A described above. The compound of Formula (1-1-b2) and the compound of Formula (1-2-b2) can be produced as a mixture by reacting the mixture of the compound of Formula (1-1-b) and the compound of Formula (1-2-b) produced by the method described in Production Method A without separation, the reaction method being the same as that in Production Method J or Production Method K. The compound of Formula (1-1-b2) and the compound of Formula (1-2-b2) can be obtained by separating and purifying the mixture by any purification methods such as recrystallization and column chromatography.

The reaction of Production Method A to Production Method K may be carried out under the atmosphere of inert gas such as nitrogen and argon, if necessary.

In the reactions of Production Method A to Production Method K, usual post-treatment of the reaction mixture after completion of the reaction such as direct concentration, concentration after dissolving in an organic solvent and washing with water, or concentration after pouring in ice-water and extracting with an organic solvent can give the compound of the present invention. When purification is required, the compound can be separated and purified by any purification method such as recrystallization and preparative isolation by column chromatography, thin layer chromatography, and liquid chromatography.

Specific examples of the active compound included in the present invention may include the compounds listed in Table 1 to Table 4. The compounds listed in Table 1 to Table 4, however, are the compounds for exemplification, and thus the present invention is not limited to these compounds. In Tables, the expression of the substituent listed in Me is methyl group. Similarly, the expression of Et is ethyl group, n-Pr and Pr-n being normal-propyl group, i-Pr and Pr-i being iso-propyl group, c-Pr and Pr-c being cyclopropyl group, n-Bu and Bu-n being normal-butyl group, s-Bu and Bu-s being secondary-butyl group, i-Bu and Bu-i being iso-butyl group, t-Bu and Bu-t being tertiary-butyl group, c-Bu and Bu-c being cyclobutyl group, n-Pen and Pen-n being normal-pentyl group, c-Pen and Pen-c being cyclopentyl group, n-Hex and Hex-n being normal-hexyl group, c-Hex and Hex-c being cyclohexyl group, n-Oct and Oct-n being octyl group, and Ph being phenyl group.

In Tables, structures of D1-2a, D1-2c, D1-7a, D1-7b-1, D1-7b-2, D1-7b-3, D1-7b-4, D1-10a, D1-11a, D1-11b-1, D1-11b-2, D1-11b-3, D1-11b-4, D1-22a, D1-22b-1, D1-22b-2, D1-22b-3, D1-22b-4, D1-32a, D1-32b-1, D1-32b-2, D1-32b-3, D1-32b-4, D1-32b-5, D1-33a, D1-33b-1, D1-33b-2, D1-33b-3, D1-33b-4, D1-34a, D1-37a, D1-37b-1, D1-108a, D1-108b-1, D1-108b-2, D1-108b-3, D1-108b-4, D1-108b-5, D1-108b-6, D1-108b-7, D1-108b-8, D1-108b-9, D1-108b-10, D1-108b-11, D1-108b-12, D1-108b-13, D1-108b-14, D1-108b-15, D1-108b-16, D1-108b-17, D1-108b-18, D1-108b-19, D1-103-1, D1-103-2, D1-103-3, D1-103-4, and A1 to A116 are the following structures.

TABLE 1

R⁶ Z^(a) Z^(b) Z^(c) A Me Me Me F H Me Me Me Cl H Me Me Me Br H Me Me Me I H Me Me Me CN H Me Me Me NO₂ H CH═CH₂ Me Me Me H c-Bu Me Me Me H c-Pen Me Me Me H c-Hex Me Me Me H Ph Me Me Me H CF₃ Me Me Me H CH₂Cl Me Me Me H CH₂OMe Me Me Me H D1-32a Me Me Me H Me Me Me Me H CH═CH₂ Me Me Me A1  CH═CH₂ Me Me Me A13 CH═CH₂ Me Me Me A14 CH═CH₂ Me Me Me A15 CH═CH₂ Me Me Me A16 CH═CH₂ Me Me Me A20 CH═CH₂ Me Me Me A23 CH═CH₂ Me Me Me A24 CH═CH₂ Me Me Me A25 CH═CH₂ Me Me Me A26 CH═CH₂ Me Me Me A27 CH═CH₂ Me Me Me A28 CH═CH₂ Me Me Me A29 CH═CH₂ Me Me Me A34 CH═CH₂ Me Me Me A35 CH═CH₂ Me Me Me A36 CH═CH₂ Me Me Me A37 CH═CH₂ Me Me Me A42 CH═CH₂ Me Me Me A58 CH═CH₂ Me Me Me A63 CH═CH₂ Me Me Me A64 CH═CH₂ Me Me Me A65 CH═CH₂ Me Me Me A67 CH═CH₂ Me Me Me A69 CH═CH₂ Me Me Me A72 CH═CH₂ Me Me Me A73 CH═CH₂ Me Me Me A74 CH═CH₂ Me Me Me A75 CH═CH₂ Me Me Me A76 CH═CH₂ Me Me Me A77 CH═CH₂ Me Me Me A81 CH═CH₂ Me Me Me A83 CH═CH₂ Me Me Me A88 CH═CH₂ Me Me Me A91 CH═CH₂ Me Me Me A97 CH═CH₂ Me Me Me A98 CH═CH₂ Me Me Me  A102 Ph Me Me Me A1  Ph Me Me Me A13 Ph Me Me Me A14 Ph Me Me Me A15 Ph Me Me Me A16 Ph Me Me Me A20 Ph Me Me Me A23 Ph Me Me Me A24 Ph Me Me Me A25 Ph Me Me Me A26 Ph Me Me Me A27 Ph Me Me Me A28 Ph Me Me Me A29 Ph Me Me Me A34 Ph Me Me Me A35 Ph Me Me Me A36 Ph Me Me Me A37 Ph Me Me Me A42 Ph Me Me Me A58 Ph Me Me Me A63 Ph Me Me Me A64 Ph Me Me Me A65 Ph Me Me Me A67 Ph Me Me Me A69 Ph Me Me Me A72 Ph Me Me Me A73 Ph Me Me Me A74 Ph Me Me Me A75 Ph Me Me Me A76 Ph Me Me Me A77 Ph Me Me Me A81 Ph Me Me Me A83 Ph Me Me Me A88 Ph Me Me Me A91 Ph Me Me Me A97 Ph Me Me Me A98 Ph Me Me Me  A102 Ph Me Me Me A1  Ph Me Me Me A13 Ph Me Me Me A14 Ph Me Me Me A15 Ph Me Me Me A16 Ph Me Me Me A20 Ph Me Me Me A23 Ph Me Me Me A24 Ph Me Me Me A25 Ph Me Me Me A26 Ph Me Me Me A27 Ph Me Me Me A28 Ph Me Me Me A29 Ph Me Me Me A34 Ph Me Me Me A35 Ph Me Me Me A36 Ph Me Me Me A37 Ph Me Me Me A42 Ph Me Me Me A58 Ph Me Me Me A63 Ph Me Me Me A64 Ph Me Me Me A65 Ph Me Me Me A67 Ph Me Me Me A69 Ph Me Me Me A72 Ph Me Me Me A73 Ph Me Me Me A74 Ph Me Me Me A75 Ph Me Me Me A76 Ph Me Me Me A77 Ph Me Me Me A81 Ph Me Me Me A83 Ph Me Me Me A88 Ph Me Me Me A91 Ph Me Me Me A97 Ph Me Me Me A98 Ph Me Me Me  A102 Ph Me Me Me  A112 Ph Me Me Me  A113 Ph Me Me Me  A114 c-Pr Me Me Me H c-Pr Me Me Me A1  c-Pr Me Me Me A2  c-Pr Me Me Me A3  c-Pr Me Me Me A4  c-Pr Me Me Me A5  c-Pr Me Me Me A6  c-Pr Me Me Me A7  c-Pr Me Me Me A8  c-Pr Me Me Me A9  c-Pr Me Me Me A10 c-Pr Me Me Me A11 c-Pr Me Me Me A12 c-Pr Me Me Me A13 c-Pr Me Me Me A14 c-Pr Me Me Me A15 c-Pr Me Me Me A16 c-Pr Me Me Me A17 c-Pr Me Me Me A18 c-Pr Me Me Me A19 c-Pr Me Me Me A20 c-Pr Me Me Me A21 c-Pr Me Me Me A22 c-Pr Me Me Me A23 c-Pr Me Me Me A24 c-Pr Me Me Me A25 c-Pr Me Me Me A26 c-Pr Me Me Me A27 c-Pr Me Me Me A28 c-Pr Me Me Me A29 c-Pr Me Me Me A30 c-Pr Me Me Me A31 c-Pr Me Me Me A32 c-Pr Me Me Me A33 c-Pr Me Me Me A34 c-Pr Me Me Me A35 c-Pr Me Me Me A36 c-Pr Me Me Me A37 c-Pr Me Me Me A38 c-Pr Me Me Me A39 c-Pr Me Me Me A40 c-Pr Me Me Me A41 c-Pr Me Me Me A42 c-Pr Me Me Me A43 c-Pr Me Me Me A44 c-Pr Me Me Me A45 c-Pr Me Me Me A46 c-Pr Me Me Me A47 c-Pr Me Me Me A48 c-Pr Me Me Me A49 c-Pr Me Me Me A50 c-Pr Me Me Me A51 c-Pr Me Me Me A52 c-Pr Me Me Me A53 c-Pr Me Me Me A54 c-Pr Me Me Me A55 c-Pr Me Me Me A56 c-Pr Me Me Me A57 c-Pr Me Me Me A58 c-Pr Me Me Me A59 c-Pr Me Me Me A60 c-Pr Me Me Me A61 c-Pr Me Me Me A62 c-Pr Me Me Me A63 c-Pr Me Me Me A64 c-Pr Me Me Me A65 c-Pr Me Me Me A66 c-Pr Me Me Me A67 c-Pr Me Me Me A68 c-Pr Me Me Me A69 c-Pr Me Me Me A70 c-Pr Me Me Me A71 c-Pr Me Me Me A72 c-Pr Me Me Me A73 c-Pr Me Me Me A74 c-Pr Me Me Me A75 c-Pr Me Me Me A76 c-Pr Me Me Me A77 c-Pr Me Me Me A78 c-Pr Me Me Me A79 c-Pr Me Me Me A80 c-Pr Me Me Me A81 c-Pr Me Me Me A82 c-Pr Me Me Me A83 c-Pr Me Me Me A84 c-Pr Me Me Me A85 c-Pr Me Me Me A86 c-Pr Me Me Me A87 c-Pr Me Me Me A88 c-Pr Me Me Me A89 c-Pr Me Me Me A90 c-Pr Me Me Me A91 c-Pr Me Me Me A92 c-Pr Me Me Me A93 c-Pr Me Me Me A94 c-Pr Me Me Me A95 c-Pr Me Me Me A96 c-Pr Me Me Me A97 c-Pr Me Me Me A98 c-Pr Me Me Me A99 c-Pr Me Me Me  A100 c-Pr Me Me Me  A101 c-Pr Me Me Me  A102 c-Pr Me Me Me  A103 c-Pr Me Me Me  A104 c-Pr Me Me Me  A105 c-Pr Me Me Me  A106 c-Pr Me Me Me  A107 c-Pr Me Me Me  A108 c-Pr Me Me Me  A109 c-Pr Me Me Me  A110 c-Pr Me Me Me  A111 c-Pr Me Me Me  A112 c-Pr Me Me Me  A113 c-Pr Me Me Me  A114 D1-108b-1 Me Me Me H D1-108b-4 Me Me Me H D1-108b-8 Me Me Me H D1-108b-16 Me Me Me H D1-108b-17 Me Me Me H D1-108b-18 Me Me Me H D1-108b-19 Me Me Me H CH₂Pr-c Me Me Me H CH₂Bu-c Me Me Me H CH₂Pen-c Me Me Me H CH₂-Hex-c Me Me Me H Me Me Me c-Pr H Me Me Me CH═CH₂ H Me Me Me CH═CHPr-n H Me Me Me CH═CHPh H Me Me Me C(O)Me H Me Me Me C(O)OMe H Me Me Me C(═NOMe)Me H Me Me Me OH H Me Me Me OMe H Me Me Me OCH₂CH₂OMe H Me Me Me OCH₂Ph H Me Me Me OCH₂(D1-34a) H Me Me Me OPh H Me Me Me O(D1-32b-1) H Me Me Me Me  A115 Me Me Me SMe H Me Me Me S(O)Me H Me Me Me S(O)₂Me H Me Me Me NHC(O)OBu-t H Me Me Me H H Me Me Me Br A1  Me Me Me Br A2  Me Me Me Br A3  Me Me Me Br A4  Me Me Me Br A5  Me Me Me Br A6  Me Me Me Br A7  Me Me Me Br A8  Me Me Me Br A9  Me Me Me Br A10 Me Me Me Br A11 Me Me Me Br A12 Me Me Me Br A13 Me Me Me Br A14 Me Me Me Br A15 Me Me Me Br A16 Me Me Me Br A17 Me Me Me Br A18 Me Me Me Br A19 Me Me Me Br A20 Me Me Me Br A21 Me Me Me Br A22 Me Me Me Br A23 Me Me Me Br A24 Me Me Me Br A25 Me Me Me Br A26 Me Me Me Br A27 Me Me Me Br A28 Me Me Me Br A29 Me Me Me Br A30 Me Me Me Br A31 Me Me Me Br A32 Me Me Me Br A33 Me Me Me Br A34 Me Me Me Br A35 Me Me Me Br A36 Me Me Me Br A37 Me Me Me Br A38 Me Me Me Br A39 Me Me Me Br A40 Me Me Me Br A41 Me Me Me Br A42 Me Me Me Br A43 Me Me Me Br A44 Me Me Me Br A45 Me Me Me Br A46 Me Me Me Br A47 Me Me Me Br A48 Me Me Me Br A49 Me Me Me Br A50 Me Me Me Br A51 Me Me Me Br A52 Me Me Me Br A53 Me Me Me Br A54 Me Me Me Br A55 Me Me Me Br A56 Me Me Me Br A57 Me Me Me Br A58 Me Me Me Br A59 Me Me Me Br A60 Me Me Me Br A61 Me Me Me Br A62 Me Me Me Br A63 Me Me Me Br A64 Me Me Me Br A65 Me Me Me Br A66 Me Me Me Br A67 Me Me Me Br A68 Me Me Me Br A69 Me Me Me Br A70 Me Me Me Br A71 Me Me Me Br A72 Me Me Me Br A73 Me Me Me Br A74 Me Me Me Br A75 Me Me Me Br A76 Me Me Me Br A77 Me Me Me Br A78 Me Me Me Br A79 Me Me Me Br A80 Me Me Me Br A81 Me Me Me Br A82 Me Me Me Br A83 Me Me Me Br A84 Me Me Me Br A85 Me Me Me Br A86 Me Me Me Br A87 Me Me Me Br A88 Me Me Me Br A89 Me Me Me Br A90 Me Me Me Br A91 Me Me Me Br A92 Me Me Me Br A93 Me Me Me Br A94 Me Me Me Br A95 Me Me Me Br A96 Me Me Me Br A97 Me Me Me Br A98 Me Me Me Br A99 Me Me Me Br  A100 Me Me Me Br  A101 Me Me Me Br  A102 Me Me Me Br  A103 Me Me Me Br  A104 Me Me Me Br  A105 Me Me Me Br  A106 Me Me Me Br  A107 Me Me Me Br  A108 Me Me Me Br  A109 Me Me Me Br  A110 Me Me Me Br  A111 Me Me Me Br  A112 Me Me Me Br  A113 Me Me Me Br  A114 Me Me Me Br  A115 Me Me Me Br  A116 Me Et Et F H Me Et Et Cl H Me Et Et Br H Me Et Et I H Me Et Et CN H Me Et Et NO₂ H CH═CH₂ Et Et Me H c-Bu Et Et Me H c-Pen Et Et Me H c-Hex Et Et Me H Ph Et Et Me H CF₃ Et Et Me H CH₂Cl Et Et Me H CH₂OMe Et Et Me H D1-32a Et Et Me H Me Et Et Me H Me Et Et Me A1  Me Et Et Me A2  Me Et Et Me A3  Me Et Et Me A4  Me Et Et Me A5  Me Et Et Me A6  Me Et Et Me A7  Me Et Et Me A8  Me Et Et Me A9  Me Et Et Me A10 Me Et Et Me A11 Me Et Et Me A12 Me Et Et Me A13 Me Et Et Me A14 Me Et Et Me A15 Me Et Et Me A16 Me Et Et Me A17 Me Et Et Me A18 Me Et Et Me A19 Me Et Et Me A20 Me Et Et Me A21 Me Et Et Me A22 Me Et Et Me A23 Me Et Et Me A24 Me Et Et Me A25 Me Et Et Me A26 Me Et Et Me A27 Me Et Et Me A28 Me Et Et Me A29 Me Et Et Me A30 Me Et Et Me A31 Me Et Et Me A32 Me Et Et Me A33 Me Et Et Me A34 Me Et Et Me A35 Me Et Et Me A36 Me Et Et Me A37 Me Et Et Me A38 Me Et Et Me A39 Me Et Et Me A40 Me Et Et Me A41 Me Et Et Me A42 Me Et Et Me A43 Me Et Et Me A44 Me Et Et Me A45 Me Et Et Me A46 Me Et Et Me A47 Me Et Et Me A48 Me Et Et Me A49 Me Et Et Me A50 Me Et Et Me A51 Me Et Et Me A52 Me Et Et Me A53 Me Et Et Me A54 Me Et Et Me A55 Me Et Et Me A56 Me Et Et Me A57 Me Et Et Me A58 Me Et Et Me A59 Me Et Et Me A60 Me Et Et Me A61 Me Et Et Me A62 Me Et Et Me A63 Me Et Et Me A64 Me Et Et Me A65 Me Et Et Me A66 Me Et Et Me A67 Me Et Et Me A68 Me Et Et Me A69 Me Et Et Me A70 Me Et Et Me A71 Me Et Et Me A72 Me Et Et Me A73 Me Et Et Me A74 Me Et Et Me A75 Me Et Et Me A76 Me Et Et Me A77 Me Et Et Me A78 Me Et Et Me A79 Me Et Et Me A80 Me Et Et Me A81 Me Et Et Me A82 Me Et Et Me A83 Me Et Et Me A84 Me Et Et Me A85 Me Et Et Me A86 Me Et Et Me A87 Me Et Et Me A88 Me Et Et Me A89 Me Et Et Me A90 Me Et Et Me A91 Me Et Et Me A92 Me Et Et Me A93 Me Et Et Me A94 Me Et Et Me A95 Me Et Et Me A96 Me Et Et Me A97 Me Et Et Me A98 Me Et Et Me A99 Me Et Et Me  A100 Me Et Et Me  A101 Me Et Et Me  A102 Me Et Et Me  A103 Me Et Et Me  A104 Me Et Et Me  A105 Me Et Et Me  A106 Me Et Et Me  A107 Me Et Et Me  A108 Me Et Et Me  A109 Me Et Et Me  A110 Me Et Et Me  A111 Me Et Et Me  A112 Me Et Et Me  A113 Me Et Et Me  A114 c-Pr Et Et Me H c-Pr Et Et Me A1  c-Pr Et Et Me A2  c-Pr Et Et Me A3  c-Pr Et Et Me A4  c-Pr Et Et Me A5  c-Pr Et Et Me A6  c-Pr Et Et Me A7  c-Pr Et Et Me A8  c-Pr Et Et Me A9  c-Pr Et Et Me A10 c-Pr Et Et Me A11 c-Pr Et Et Me A12 c-Pr Et Et Me A13 c-Pr Et Et Me A14 c-Pr Et Et Me A15 c-Pr Et Et Me A16 c-Pr Et Et Me A17 c-Pr Et Et Me A18 c-Pr Et Et Me A19 c-Pr Et Et Me A20 c-Pr Et Et Me A21 c-Pr Et Et Me A22 c-Pr Et Et Me A23 c-Pr Et Et Me A24 c-Pr Et Et Me A25 c-Pr Et Et Me A26 c-Pr Et Et Me A27 c-Pr Et Et Me A28 c-Pr Et Et Me A29 c-Pr Et Et Me A30 c-Pr Et Et Me A31 c-Pr Et Et Me A32 c-Pr Et Et Me A33 c-Pr Et Et Me A34 c-Pr Et Et Me A35 c-Pr Et Et Me A36 c-Pr Et Et Me A37 c-Pr Et Et Me A38 c-Pr Et Et Me A39 c-Pr Et Et Me A40 c-Pr Et Et Me A41 c-Pr Et Et Me A42 c-Pr Et Et Me A43 c-Pr Et Et Me A44 c-Pr Et Et Me A45 c-Pr Et Et Me A46 c-Pr Et Et Me A47 c-Pr Et Et Me A48 c-Pr Et Et Me A49 c-Pr Et Et Me A50 c-Pr Et Et Me A51 c-Pr Et Et Me A52 c-Pr Et Et Me A53 c-Pr Et Et Me A54 c-Pr Et Et Me A55 c-Pr Et Et Me A56 c-Pr Et Et Me A57 c-Pr Et Et Me A58 c-Pr Et Et Me A59 c-Pr Et Et Me A60 c-Pr Et Et Me A61 c-Pr Et Et Me A62 c-Pr Et Et Me A63 c-Pr Et Et Me A64 c-Pr Et Et Me A65 c-Pr Et Et Me A66 c-Pr Et Et Me A67 c-Pr Et Et Me A68 c-Pr Et Et Me A69 c-Pr Et Et Me A70 c-Pr Et Et Me A71 c-Pr Et Et Me A72 c-Pr Et Et Me A73 c-Pr Et Et Me A74 c-Pr Et Et Me A75 c-Pr Et Et Me A76 c-Pr Et Et Me A77 c-Pr Et Et Me A78 c-Pr Et Et Me A79 c-Pr Et Et Me A80 c-Pr Et Et Me A81 c-Pr Et Et Me A82 c-Pr Et Et Me A83 c-Pr Et Et Me A84 c-Pr Et Et Me A85 c-Pr Et Et Me A86 c-Pr Et Et Me A87 c-Pr Et Et Me A88 c-Pr Et Et Me A89 c-Pr Et Et Me A90 c-Pr Et Et Me A91 c-Pr Et Et Me A92 c-Pr Et Et Me A93 c-Pr Et Et Me A94 c-Pr Et Et Me A95 c-Pr Et Et Me A96 c-Pr Et Et Me A97 c-Pr Et Et Me A98 c-Pr Et Et Me A99 c-Pr Et Et Me  A100 c-Pr Et Et Me  A101 c-Pr Et Et Me  A102 c-Pr Et Et Me  A103 c-Pr Et Et Me  A104 c-Pr Et Et Me  A105 c-Pr Et Et Me  A106 c-Pr Et Et Me  A107 c-Pr Et Et Me  A108 c-Pr Et Et Me  A109 c-Pr Et Et Me  A110 c-Pr Et Et Me  A111 c-Pr Et Et Me  A112 c-Pr Et Et Me  A113 c-Pr Et Et Me  A114 D1-108b-1 Et Et Me H D1-108b-4 Et Et Me H D1-108b-8 Et Et Me H D1-108b-16 Et Et Me H D1-108b-17 Et Et Me H D1-108b-18 Et Et Me H D1-108b-19 Et Et Me H CH₂Pr-c Et Et Me H CH₂Bu-c Et Et Me H CH₂Pen-c Et Et Me H CH₂-Hex-c Et Et Me H Me Et Et c-Pr H Me Et Et CH═CH₂ H Me Et Et CH═CHPr-n H Me Et Et CH═CHPh H Me Et Et C(O)Me H Me Et Et C(O)OMe H Me Et Et C(═NOMe)Me H Me Et Et OH H Me Et Et OMe H Me Et Et OCH₂CH₂OMe H Me Et Et OCH₂Ph H Me Et Et OCH₂(D1-34a) H Me Et Et OPh H Me Et Et O(D1-32b-1) H Me Et Et Me  A115 Me Et Et SMe H Me Et Et S(O)Me H Me Et Et S(O)₂Me H Me Et Et NHC(O)OBu-t H Me Et Et H H Me Et Et Br A1  Me Et Et Br A2  Me Et Et Br A3  Me Et Et Br A4  Me Et Et Br A5  Me Et Et Br A6  Me Et Et Br A7  Me Et Et Br A8  Me Et Et Br A9  Me Et Et Br A10 Me Et Et Br A11 Me Et Et Br A12 Me Et Et Br A13 Me Et Et Br A14 Me Et Et Br A15 Me Et Et Br A16 Me Et Et Br A17 Me Et Et Br A18 Me Et Et Br A19 Me Et Et Br A20 Me Et Et Br A21 Me Et Et Br A22 Me Et Et Br A23 Me Et Et Br A24 Me Et Et Br A25 Me Et Et Br A26 Me Et Et Br A27 Me Et Et Br A28 Me Et Et Br A29 Me Et Et Br A30 Me Et Et Br A31 Me Et Et Br A32 Me Et Et Br A33 Me Et Et Br A34 Me Et Et Br A35 Me Et Et Br A36 Me Et Et Br A37 Me Et Et Br A38 Me Et Et Br A39 Me Et Et Br A40 Me Et Et Br A41 Me Et Et Br A42 Me Et Et Br A43 Me Et Et Br A44 Me Et Et Br A45 Me Et Et Br A46 Me Et Et Br A47 Me Et Et Br A48 Me Et Et Br A49 Me Et Et Br A50 Me Et Et Br A51 Me Et Et Br A52 Me Et Et Br A53 Me Et Et Br A54 Me Et Et Br A55 Me Et Et Br A56 Me Et Et Br A57 Me Et Et Br A58 Me Et Et Br A59 Me Et Et Br A60 Me Et Et Br A61 Me Et Et Br A62 Me Et Et Br A63 Me Et Et Br A64 Me Et Et Br A65 Me Et Et Br A66 Me Et Et Br A67 Me Et Et Br A68 Me Et Et Br A69 Me Et Et Br A70 Me Et Et Br A71 Me Et Et Br A72 Me Et Et Br A73 Me Et Et Br A74 Me Et Et Br A75 Me Et Et Br A76 Me Et Et Br A77 Me Et Et Br A78 Me Et Et Br A79 Me Et Et Br A80 Me Et Et Br A81 Me Et Et Br A82 Me Et Et Br A83 Me Et Et Br A84 Me Et Et Br A85 Me Et Et Br A86 Me Et Et Br A87 Me Et Et Br A88 Me Et Et Br A89 Me Et Et Br A90 Me Et Et Br A91 Me Et Et Br A92 Me Et Et Br A93 Me Et Et Br A94 Me Et Et Br A95 Me Et Et Br A96 Me Et Et Br A97 Me Et Et Br A98 Me Et Et Br A99 Me Et Et Br  A100 Me Et Et Br  A101 Me Et Et Br  A102 Me Et Et Br  A103 Me Et Et Br  A104 Me Et Et Br  A105 Me Et Et Br  A106 Me Et Et Br  A107 Me Et Et Br  A108 Me Et Et Br  A109 Me Et Et Br  A110 Me Et Et Br  A111 Me Et Et Br  A112 Me Et Et Br  A113 Me Et Et Br  A114 Me Et Et Br  A115 Me Et Et Br  A116 H Me Me F H H Me Me Cl H H Me Me Br H H Me Me I H H Me Me CN H H Me Me NO₂ H H Me Me Me H H Me Me Me A1  H Me Me Me A2  H Me Me Me A3  H Me Me Me A4  H Me Me Me A5  H Me Me Me A6  H Me Me Me A7  H Me Me Me A8  H Me Me Me A9  H Me Me Me A10 H Me Me Me A11 H Me Me Me A12 H Me Me Me A13 H Me Me Me A14 H Me Me Me A15 H Me Me Me A16 H Me Me Me A17 H Me Me Me A18 H Me Me Me A19 H Me Me Me A20 H Me Me Me A21 H Me Me Me A22 H Me Me Me A23 H Me Me Me A24 H Me Me Me A25 H Me Me Me A26 H Me Me Me A27 H Me Me Me A28 H Me Me Me A29 H Me Me Me A30 H Me Me Me A31 H Me Me Me A32 H Me Me Me A33 H Me Me Me A34 H Me Me Me A35 H Me Me Me A36 H Me Me Me A37 H Me Me Me A38 H Me Me Me A39 H Me Me Me A40 H Me Me Me A41 H Me Me Me A42 H Me Me Me A43 H Me Me Me A44 H Me Me Me A45 H Me Me Me A46 H Me Me Me A47 H Me Me Me A48 H Me Me Me A49 H Me Me Me A50 H Me Me Me A51 H Me Me Me A52 H Me Me Me A53 H Me Me Me A54 H Me Me Me A55 H Me Me Me A56 H Me Me Me A57 H Me Me Me A58 H Me Me Me A59 H Me Me Me A60 H Me Me Me A61 H Me Me Me A62 H Me Me Me A63 H Me Me Me A64 H Me Me Me A65 H Me Me Me A66 H Me Me Me A67 H Me Me Me A68 H Me Me Me A69 H Me Me Me A70 H Me Me Me A71 H Me Me Me A72 H Me Me Me A73 H Me Me Me A74 H Me Me Me A75 H Me Me Me A76 H Me Me Me A77 H Me Me Me A78 H Me Me Me A79 H Me Me Me A80 H Me Me Me A81 H Me Me Me A82 H Me Me Me A83 H Me Me Me A84 H Me Me Me A85 H Me Me Me A86 H Me Me Me A87 H Me Me Me A88 H Me Me Me A89 H Me Me Me A90 H Me Me Me A91 H Me Me Me A92 H Me Me Me A93 H Me Me Me A94 H Me Me Me A95 H Me Me Me A96 H Me Me Me A97 H Me Me Me A98 H Me Me Me A99 H Me Me Me  A100 H Me Me Me  A101 H Me Me Me  A102 H Me Me Me  A103 H Me Me Me  A104 H Me Me Me  A105 H Me Me Me  A106 H Me Me c-Pr H H Me Me CH═CH₂ H H Me Me CH═CHPr-n H H Me Me CH═CHPh H H Me Me C(O)Me H H Me Me C(O)OMe H H Me Me C(═NOMe)Me H H Me Me OH H H Me Me OMe H H Me Me OCH₂CH₂OMe H H Me Me OCH₂Ph H H Me Me OCH₂(D1-34a) H H Me Me OPh H H Me Me O(D1-32b-1) H H Me Me Me H H Me Me SMe H H Me Me S(O)Me H H Me Me S(O)₂Me H H Me Me NHC(O)OBu-t H Me Me Me Me A116 Me Me Et Me A116 CF₃ Me Me Me A1  CF₃ Me Me Me A13 CF₃ Me Me Me A14 CF₃ Me Me Me A15 CF₃ Me Me Me A16 CF₃ Me Me Me A20 CF₃ Me Me Me A23 CF₃ Me Me Me A24 CF₃ Me Me Me A25 CF₃ Me Me Me A26 CF₃ Me Me Me A27 CF₃ Me Me Me A28 CF₃ Me Me Me A29 CF₃ Me Me Me A34 CF₃ Me Me Me A35 CF₃ Me Me Me A36 CF₃ Me Me Me A37 CF₃ Me Me Me A42 CF3 Me Me Me A58 CF3 Me Me Me A63 CF3 Me Me Me A64 CF3 Me Me Me A65 CF₃ Me Me Me A67 CF₃ Me Me Me A69 CF₃ Me Me Me A72 CF₃ Me Me Me A73 CF₃ Me Me Me A74 CF₃ Me Me Me A75 CF₃ Me Me Me A76 CF₃ Me Me Me A77 CF₃ Me Me Me A81 CF₃ Me Me Me A83 CF₃ Me Me Me A88 CF₃ Me Me Me A91 CF₃ Me Me Me A97 CF₃ Me Me Me A98 CF₃ Me Me Me  A102 D1-32a Me Me Me A1  D1-32a Me Me Me A13 D1-32a Me Me Me A14 D1-32a Me Me Me A15 D1-32a Me Me Me A16 D1-32a Me Me Me A20 D1-32a Me Me Me A23 D1-32a Me Me Me A24 D1-32a Me Me Me A25 D1-32a Me Me Me A26 D1-32a Me Me Me A27 D1-32a Me Me Me A28 D1-32a Me Me Me A29 D1-32a Me Me Me A34 D1-32a Me Me Me A35 D1-32a Me Me Me A36 D1-32a Me Me Me A37 D1-32a Me Me Me A42 D1-32a Me Me Me A58 D1-32a Me Me Me A63 D1-32a Me Me Me A64 D1-32a Me Me Me A65 D1-32a Me Me Me A67 D1-32a Me Me Me A69 D1-32a Me Me Me A72 D1-32a Me Me Me A73 D1-32a Me Me Me A74 D1-32a Me Me Me A75 D1-32a Me Me Me A76 D1-32a Me Me Me A77 D1-32a Me Me Me A81 D1-32a Me Me Me A83 D1-32a Me Me Me A88 D1-32a Me Me Me A91 D1-32a Me Me Me A97 D1-32a Me Me Me A98 D1-32a Me Me Me  A102 CH₂Pr-c Me Me Me A1  CH₂Pr-c Me Me Me A13 CH₂Pr-c Me Me Me A14 CH₂Pr-c Me Me Me A15 CH₂Pr-c Me Me Me A16 CH₂Pr-c Me Me Me A20 CH₂Pr-c Me Me Me A23 CH₂Pr-c Me Me Me A24 CH₂Pr-c Me Me Me A25 CH₂Pr-c Me Me Me A26 CH₂Pr-c Me Me Me A27 CH₂Pr-c Me Me Me A28 CH₂Pr-c Me Me Me A29 CH₂Pr-c Me Me Me A34 CH₂Pr-c Me Me Me A35 CH₂Pr-c Me Me Me A36 CH₂Pr-c Me Me Me A37 CH₂Pr-c Me Me Me A42 CH₂Pr-c Me Me Me A58 CH₂Pr-c Me Me Me A63 CH₂Pr-c Me Me Me A64 CH₂Pr-c Me Me Me A65 CH₂Pr-c Me Me Me A67 CH₂Pr-c Me Me Me A69 CH₂Pr-c Me Me Me A72 CH₂Pr-c Me Me Me A73 CH₂Pr-c Me Me Me A74 CH₂Pr-c Me Me Me A75 CH₂Pr-c Me Me Me A76 CH₂Pr-c Me Me Me A77 CH₂Pr-c Me Me Me A81 CH₂Pr-c Me Me Me A83 CH₂Pr-c Me Me Me A88 CH₂Pr-c Me Me Me A91 CH₂Pr-c Me Me Me A97 CH₂Pr-c Me Me Me A98 CH₂Pr-c Me Me Me  A102 D1-108b-4 Me Me Me A1  D1-108b-4 Me Me Me A13 D1-108b-4 Me Me Me A14 D1-108b-4 Me Me Me A15 D1-108b-4 Me Me Me A16 D1-108b-4 Me Me Me A20 D1-108b-4 Me Me Me A23 D1-108b-4 Me Me Me A24 D1-108b-4 Me Me Me A25 D1-108b-4 Me Me Me A26 D1-108b-4 Me Me Me A27 D1-108b-4 Me Me Me A28 D1-108b-4 Me Me Me A29 D1-108b-4 Me Me Me A34 D1-108b-4 Me Me Me A35 D1-108b-4 Me Me Me A36 D1-108b-4 Me Me Me A37 D1-108b-4 Me Me Me A42 D1-108b-4 Me Me Me A58 D1-108b-4 Me Me Me A63 D1-108b-4 Me Me Me A64 D1-108b-4 Me Me Me A65 D1-108b-4 Me Me Me A67 D1-108b-4 Me Me Me A69 D1-108b-4 Me Me Me A72 D1-108b-4 Me Me Me A73 D1-108b-4 Me Me Me A74 D1-108b-4 Me Me Me A75 D1-108b-4 Me Me Me A76 D1-108b-4 Me Me Me A77 D1-108b-4 Me Me Me A81 D1-108b-4 Me Me Me A83 D1-108b-4 Me Me Me A88 D1-108b-4 Me Me Me A91 D1-108b-4 Me Me Me A97 D1-108b-4 Me Me Me A98 D1-108b-4 Me Me Me  A102 Me Me Me NO₂ A1  Me Me Me NO₂ A13 Me Me Me NO₂ A14 Me Me Me NO₂ A15 Me Me Me NO₂ A16 Me Me Me NO₂ A20 Me Me Me NO₂ A23 Me Me Me NO₂ A24 Me Me Me NO₂ A25 Me Me Me NO₂ A26 Me Me Me NO₂ A27 Me Me Me NO₂ A28 Me Me Me NO₂ A29 Me Me Me NO₂ A34 Me Me Me NO₂ A35 Me Me Me NO₂ A36 Me Me Me NO₂ A37 Me Me Me NO₂ A42 Me Me Me NO₂ A58 Me Me Me NO₂ A63 Me Me Me NO₂ A64 Me Me Me NO₂ A65 Me Me Me NO₂ A67 Me Me Me NO₂ A69 Me Me Me NO₂ A72 Me Me Me NO₂ A73 Me Me Me NO₂ A74 Me Me Me NO₂ A75 Me Me Me NO₂ A76 Me Me Me NO₂ A77 Me Me Me NO₂ A81 Me Me Me NO₂ A83 Me Me Me NO₂ A88 Me Me Me NO₂ A91 Me Me Me NO₂ A97 Me Me Me NO₂ A98 Me Me Me NO₂  A102 Me Me Me CH═CH₂ A1  Me Me Me CH═CH₂ A13 Me Me Me CH═CH₂ A14 Me Me Me CH═CH₂ A15 Me Me Me CH═CH₂ A16 Me Me Me CH═CH₂ A20 Me Me Me CH═CH₂ A23 Me Me Me CH═CH₂ A24 Me Me Me CH═CH₂ A25 Me Me Me CH═CH₂ A26 Me Me Me CH═CH₂ A27 Me Me Me CH═CH₂ A28 Me Me Me CH═CH₂ A29 Me Me Me CH═CH₂ A34 Me Me Me CH═CH₂ A35 Me Me Me CH═CH₂ A36 Me Me Me CH═CH₂ A37 Me Me Me CH═CH₂ A42 Me Me Me CH═CH₂ A58 Me Me Me CH═CH₂ A63 Me Me Me CH═CH₂ A64 Me Me Me CH═CH₂ A65 Me Me Me CH═CH₂ A67 Me Me Me CH═CH₂ A69 Me Me Me CH═CH₂ A72 Me Me Me CH═CH₂ A73 Me Me Me CH═CH₂ A74 Me Me Me CH═CH₂ A75 Me Me Me CH═CH₂ A76 Me Me Me CH═CH₂ A77 Me Me Me CH═CH₂ A81 Me Me Me CH═CH₂ A83 Me Me Me CH═CH₂ A88 Me Me Me CH═CH₂ A91 Me Me Me CH═CH₂ A97 Me Me Me CH═CH₂ A98 Me Me Me CH═CH₂  A102 Me Me Me C(O)Me A1  Me Me Me C(O)Me A13 Me Me Me C(O)Me A14 Me Me Me C(O)Me A15 Me Me Me C(O)Me A16 Me Me Me C(O)Me A20 Me Me Me C(O)Me A23 Me Me Me C(O)Me A24 Me Me Me C(O)Me A25 Me Me Me C(O)Me A26 Me Me Me C(O)Me A27 Me Me Me C(O)Me A28 Me Me Me C(O)Me A29 Me Me Me C(O)Me A34 Me Me Me C(O)Me A35 Me Me Me C(O)Me A36 Me Me Me C(O)Me A37 Me Me Me C(O)Me A42 Me Me Me C(O)Me A58 Me Me Me C(O)Me A63 Me Me Me C(O)Me A64 Me Me Me C(O)Me A65 Me Me Me C(O)Me A67 Me Me Me C(O)Me A69 Me Me Me C(O)Me A72 Me Me Me C(O)Me A73 Me Me Me C(O)Me A74 Me Me Me C(O)Me A75 Me Me Me C(O)Me A76 Me Me Me C(O)Me A77 Me Me Me C(O)Me A81 Me Me Me C(O)Me A83 Me Me Me C(O)Me A88 Me Me Me C(O)Me A91 Me Me Me C(O)Me A97 Me Me Me C(O)Me A98 Me Me Me C(═NOMe)Me A1  Me Me Me C(═NOMe)Me A13 Me Me Me C(═NOMe)Me A14 Me Me Me C(═NOMe)Me A15 Me Me Me C(═NOMe)Me A16 Me Me Me C(═NOMe)Me A20 Me Me Me C(═NOMe)Me A23 Me Me Me C(═NOMe)Me A24 Me Me Me C(═NOMe)Me A25 Me Me Me C(═NOMe)Me A26 Me Me Me C(═NOMe)Me A27 Me Me Me C(═NOMe)Me A28 Me Me Me C(═NOMe)Me A29 Me Me Me C(═NOMe)Me A34 Me Me Me C(═NOMe)Me A35 Me Me Me C(═NOMe)Me A36 Me Me Me C(═NOMe)Me A37 Me Me Me C(═NOMe)Me A42 Me Me Me C(═NOMe)Me A58 Me Me Me C(═NOMe)Me A63 Me Me Me C(═NOMe)Me A64 Me Me Me C(═NOMe)Me A65 Me Me Me C(═NOMe)Me A67 Me Me Me C(═NOMe)Me A69 Me Me Me C(═NOMe)Me A72 Me Me Me C(═NOMe)Me A73 Me Me Me C(═NOMe)Me A74 Me Me Me C(═NOMe)Me A75 Me Me Me C(═NOMe)Me A76 Me Me Me C(═NOMe)Me A77 Me Me Me C(═NOMe)Me A81 Me Me Me C(═NOMe)Me A83 Me Me Me C(═NOMe)Me A88 Me Me Me C(═NOMe)Me A91 Me Me Me C(═NOMe)Me A97 Me Me Me C(═NOMe)Me A98 Me Me Me C(═NOMe)Me  A102 Me Me Me OMe A1  Me Me Me OMe A13 Me Me Me OMe A14 Me Me Me OMe A15 Me Me Me OMe A16 Me Me Me OMe A20 Me Me Me OMe A23 Me Me Me OMe A24 Me Me Me OMe A25 Me Me Me OMe A26 Me Me Me OMe A27 Me Me Me OMe A28 Me Me Me OMe A29 Me Me Me OMe A34 Me Me Me OMe A35 Me Me Me OMe A36 Me Me Me OMe A37 Me Me Me OMe A42 Me Me Me OMe A58 Me Me Me OMe A63 Me Me Me OMe A64 Me Me Me OMe A65 Me Me Me OMe A67 Me Me Me OMe A69 Me Me Me OMe A72 Me Me Me OMe A73 Me Me Me OMe A74 Me Me Me OMe A75 Me Me Me OMe A76 Me Me Me OMe A77 Me Me Me OMe A81 Me Me Me OMe A83 Me Me Me OMe A88 Me Me Me OMe A91 Me Me Me OMe A97 Me Me Me OMe A98 Me Me Me OMe  A102 Me Me Me OCH₂Ph A1  Me Me Me OCH₂Ph A13 Me Me Me OCH₂Ph A14 Me Me Me OCH₂Ph A15 Me Me Me OCH₂Ph A16 Me Me Me OCH₂Ph A20 Me Me Me OCH₂Ph A23 Me Me Me OCH₂Ph A24 Me Me Me OCH₂Ph A25 Me Me Me OCH₂Ph A26 Me Me Me OCH₂Ph A27 Me Me Me OCH₂Ph A28 Me Me Me OCH₂Ph A29 Me Me Me OCH₂Ph A34 Me Me Me OCH₂Ph A35 Me Me Me OCH₂Ph A36 Me Me Me OCH₂Ph A37 Me Me Me OCH₂Ph A42 Me Me Me OCH₂Ph A58 Me Me Me OCH₂Ph A63 Me Me Me OCH₂Ph A64 Me Me Me OCH₂Ph A65 Me Me Me OCH₂Ph A67 Me Me Me OCH₂Ph A69 Me Me Me OCH₂Ph A72 Me Me Me OCH₂Ph A73 Me Me Me OCH₂Ph A74 Me Me Me OCH₂Ph A75 Me Me Me OCH₂Ph A76 Me Me Me OCH₂Ph A77 Me Me Me OCH₂Ph A81 Me Me Me OCH₂Ph A83 Me Me Me OCH₂Ph A88 Me Me Me OCH₂Ph A91 Me Me Me OCH₂Ph A97 Me Me Me OCH₂Ph A98 Me Me Me OCH₂Ph  A102 Me Me Me OPh A1  Me Me Me OPh A13 Me Me Me OPh A14 Me Me Me OPh A15 Me Me Me OPh A16 Me Me Me OPh A20 Me Me Me OPh A23 Me Me Me OPh A24 Me Me Me OPh A25 Me Me Me OPh A26 Me Me Me OPh A27 Me Me Me OPh A28 Me Me Me OPh A29 Me Me Me OPh A34 Me Me Me OPh A35 Me Me Me OPh A36 Me Me Me OPh A37 Me Me Me OPh A42 Me Me Me OPh A58 Me Me Me OPh A63 Me Me Me OPh A64 Me Me Me OPh A65 Me Me Me OPh A67 Me Me Me OPh A69 Me Me Me OPh A72 Me Me Me OPh A73 Me Me Me OPh A74 Me Me Me OPh A75 Me Me Me OPh A76 Me Me Me OPh A77 Me Me Me OPh A81 Me Me Me OPh A83 Me Me Me OPh A88 Me Me Me OPh A91 Me Me Me OPh A97 Me Me Me OPh A98 Me Me Me OPh  A102 Me Me Me SMe A1  Me Me Me SMe A13 Me Me Me SMe A14 Me Me Me SMe A15 Me Me Me SMe A16 Me Me Me SMe A20 Me Me Me SMe A23 Me Me Me SMe A24 Me Me Me SMe A25 Me Me Me SMe A26 Me Me Me SMe A27 Me Me Me SMe A28 Me Me Me SMe A29 Me Me Me SMe A34 Me Me Me SMe A35 Me Me Me SMe A36 Me Me Me SMe A37 Me Me Me SMe A42 Me Me Me SMe A58 Me Me Me SMe A63 Me Me Me SMe A64 Me Me Me SMe A65 Me Me Me SMe A67 Me Me Me SMe A69 Me Me Me SMe A72 Me Me Me SMe A73 Me Me Me SMe A74 Me Me Me SMe A75 Me Me Me SMe A76 Me Me Me SMe A77 Me Me Me SMe A81 Me Me Me SMe A83 Me Me Me SMe A88 Me Me Me SMe A91 Me Me Me SMe A97 Me Me Me SMe A98 Me Me Me SMe  A102 Me Me Me Me A1  Me Me Me Me A2  Me Me Me Me A3  Me Me Me Me A4  Me Me Me Me A5  Me Me Me Me A6  Me Me Me Me A7  Me Me Me Me A8  Me Me Me Me A9  Me Me Me Me A10 Me Me Me Me A11 Me Me Me Me A12 Me Me Me Me A13 Me Me Me Me A14 Me Me Me Me A15 Me Me Me Me A16 Me Me Me Me A17 Me Me Me Me A18 Me Me Me Me A19 Me Me Me Me A20 Me Me Me Me A21 Me Me Me Me A22 Me Me Me Me A23 Me Me Me Me A24 Me Me Me Me A25 Me Me Me Me A26 Me Me Me Me A27 Me Me Me Me A28 Me Me Me Me A29 Me Me Me Me A30 Me Me Me Me A31 Me Me Me Me A32 Me Me Me Me A33 Me Me Me Me A34 Me Me Me Me A35 Me Me Me Me A36 Me Me Me Me A37 Me Me Me Me A38 Me Me Me Me A39 Me Me Me Me A40 Me Me Me Me A41 Me Me Me Me A42 Me Me Me Me A43 Me Me Me Me A44 Me Me Me Me A45 Me Me Me Me A46 Me Me Me Me A47 Me Me Me Me A48 Me Me Me Me A49 Me Me Me Me A50 Me Me Me Me A51 Me Me Me Me A52 Me Me Me Me A53 Me Me Me Me A54 Me Me Me Me A55 Me Me Me Me A56 Me Me Me Me A57 Me Me Me Me A58 Me Me Me Me A59 Me Me Me Me A60 Me Me Me Me A61 Me Me Me Me A62 Me Me Me Me A63 Me Me Me Me A64 Me Me Me Me A65 Me Me Me Me A66 Me Me Me Me A67 Me Me Me Me A68 Me Me Me Me A69 Me Me Me Me A70 Me Me Me Me A71 Me Me Me Me A72 Me Me Me Me A73 Me Me Me Me A74 Me Me Me Me A75 Me Me Me Me A76 Me Me Me Me A77 Me Me Me Me A78 Me Me Me Me A79 Me Me Me Me A80 Me Me Me Me A81 Me Me Me Me A82 Me Me Me Me A83 Me Me Me Me A84 Me Me Me Me A85 Me Me Me Me A86 Me Me Me Me A87 Me Me Me Me A88 Me Me Me Me A89 Me Me Me Me A90 Me Me Me Me A91 Me Me Me Me A92 Me Me Me Me A93 Me Me Me Me A94 Me Me Me Me A95 Me Me Me Me A96 Me Me Me Me A97 Me Me Me Me A98 Me Me Me Me A99 Me Me Me Me A100  Me Me Me Me A101  Me Me Me Me A102  Me Me Me Me A103  Me Me Me Me A104  Me Me Me Me A105  Me Me Me Me A106  Me Me Me Me A107  Me Me Me Me A108  Me Me Me Me A109  Me Me Me Me A110  Me Me Me Me A111  Me Me Me Me A112  Me Me Me Me A113  Me Me Me Me A114  Me Me Me Me A115  Me Me Me D1-103-1 H Me Me Me D1-103-2 H Me Me Me D1-103-3 H Me Me Me D1-103-4 H Me Et Et D1-103-1 H Me Et Et D1-103-2 H Me Et Et D1-103-3 H Me Et Et D1-103-4 H Me Me Et F H Me Me Et Cl H Me Me Et Br H Me Me Et I H Me Me Et CN H Me Me Et NO₂ H CH═CH₂ Me Et Me H c-Bu Me Et Me H c-Pen Me Et Me H c-Hex Me Et Me H Ph Me Et Me H CF₃ Me Et Me H CH₂Cl Me Et Me H CH₂OMe Me Et Me H D1-32a Me Et Me H Me Me Et Me H Me Me Et Me A1  Me Me Et Me A13 Me Me Et Me A14 Me Me Et Me A15 Me Me Et Me A16 Me Me Et Me A20 Me Me Et Me A23 Me Me Et Me A24 Me Me Et Me A25 Me Me Et Me A26 Me Me Et Me A27 Me Me Et Me A28 Me Me Et Me A29 Me Me Et Me A30 Me Me Et Me A31 Me Me Et Me A32 Me Me Et Me A33 Me Me Et Me A34 Me Me Et Me A35 Me Me Et Me A36 Me Me Et Me A37 Me Me Et Me A38 Me Me Et Me A39 Me Me Et Me A40 Me Me Et Me A41 Me Me Et Me A42 Me Me Et Me A42 Me Me Et Me A44 Me Me Et Me A45 Me Me Et Me A46 Me Me Et Me A47 Me Me Et Me A48 Me Me Et Me A49 Me Me Et Me A50 Me Me Et Me A51 Me Me Et Me A52 Me Me Et Me A53 Me Me Et Me A54 Me Me Et Me A55 Me Me Et Me A56 Me Me Et Me A57 Me Me Et Me A58 Me Me Et Me A59 Me Me Et Me A60 Me Me Et Me A61 Me Me Et Me A62 Me Me Et Me A63 Me Me Et Me A64 Me Me Et Me A65 Me Me Et Me A66 Me Me Et Me A67 Me Me Et Me A68 Me Me Et Me A69 Me Me Et Me A70 Me Me Et Me A71 Me Me Et Me A72 Me Me Et Me A73 Me Me Et Me A74 Me Me Et Me A75 Me Me Et Me A76 Me Me Et Me A77 Me Me Et Me A78 Me Me Et Me A79 Me Me Et Me A80 Me Me Et Me A81 Me Me Et Me A82 Me Me Et Me A83 Me Me Et Me A84 Me Me Et Me A85 Me Me Et Me A86 Me Me Et Me A87 Me Me Et Me A88 Me Me Et Me A89 Me Me Et Me A90 Me Me Et Me A91 Me Me Et Me A92 Me Me Et Me A93 Me Me Et Me A94 Me Me Et Me A95 Me Me Et Me A96 Me Me Et Me A97 Me Me Et Me A98 Me Me Et Me A99 Me Me Et Me A100  Me Me Et Me A101  Me Me Et Me A102  Me Me Et Me A103  Me Me Et Me A104  Me Me Et Me A105  Me Me Et Me A106  Me Me Et Me A107  Me Me Et Me A108  Me Me Et Me A109  Me Me Et Me A110  Me Me Et Me A111  Me Me Et Me A112  Me Me Et Me A113  Me Me Et Me A114  c-Pr Me Et Me H c-Pr Me Et Me A1  c-Pr Me Et Me A2  c-Pr Me Et Me A3  c-Pr Me Et Me A4  c-Pr Me Et Me A5  c-Pr Me Et Me A6  c-Pr Me Et Me A7  c-Pr Me Et Me A8  c-Pr Me Et Me A9  c-Pr Me Et Me A10 c-Pr Me Et Me A11 c-Pr Me Et Me A12 c-Pr Me Et Me A13 c-Pr Me Et Me A14 c-Pr Me Et Me A15 c-Pr Me Et Me A16 c-Pr Me Et Me A17 c-Pr Me Et Me A18 c-Pr Me Et Me A19 c-Pr Me Et Me A20 c-Pr Me Et Me A21 c-Pr Me Et Me A22 c-Pr Me Et Me A23 c-Pr Me Et Me A24 c-Pr Me Et Me A25 c-Pr Me Et Me A26 c-Pr Me Et Me A27 c-Pr Me Et Me A28 c-Pr Me Et Me A29 c-Pr Me Et Me A30 c-Pr Me Et Me A31 c-Pr Me Et Me A32 c-Pr Me Et Me A33 c-Pr Me Et Me A34 c-Pr Me Et Me A35 c-Pr Me Et Me A36 c-Pr Me Et Me A37 c-Pr Me Et Me A38 c-Pr Me Et Me A39 c-Pr Me Et Me A40 c-Pr Me Et Me A41 c-Pr Me Et Me A42 c-Pr Me Et Me A43 c-Pr Me Et Me A44 c-Pr Me Et Me A45 c-Pr Me Et Me A46 c-Pr Me Et Me A47 c-Pr Me Et Me A48 c-Pr Me Et Me A49 c-Pr Me Et Me A50 c-Pr Me Et Me A51 c-Pr Me Et Me A52 c-Pr Me Et Me A53 c-Pr Me Et Me A54 c-Pr Me Et Me A55 c-Pr Me Et Me A56 c-Pr Me Et Me A57 c-Pr Me Et Me A58 c-Pr Me Et Me A59 c-Pr Me Et Me A60 c-Pr Me Et Me A61 c-Pr Me Et Me A62 c-Pr Me Et Me A63 c-Pr Me Et Me A64 c-Pr Me Et Me A65 c-Pr Me Et Me A66 c-Pr Me Et Me A67 c-Pr Me Et Me A68 c-Pr Me Et Me A69 c-Pr Me Et Me A70 c-Pr Me Et Me A71 c-Pr Me Et Me A72 c-Pr Me Et Me A73 c-Pr Me Et Me A74 c-Pr Me Et Me A75 c-Pr Me Et Me A76 c-Pr Me Et Me A77 c-Pr Me Et Me A78 c-Pr Me Et Me A79 c-Pr Me Et Me A80 c-Pr Me Et Me A81 c-Pr Me Et Me A82 c-Pr Me Et Me A83 c-Pr Me Et Me A84 c-Pr Me Et Me A85 c-Pr Me Et Me A86 c-Pr Me Et Me A87 c-Pr Me Et Me A88 c-Pr Me Et Me A89 c-Pr Me Et Me A90 c-Pr Me Et Me A91 c-Pr Me Et Me A92 c-Pr Me Et Me A93 c-Pr Me Et Me A94 c-Pr Me Et Me A95 c-Pr Me Et Me A96 c-Pr Me Et Me A97 c-Pr Me Et Me A98 c-Pr Me Et Me A99 c-Pr Me Et Me  A100 c-Pr Me Et Me  A101 c-Pr Me Et Me  A102 c-Pr Me Et Me  A103 c-Pr Me Et Me  A104 c-Pr Me Et Me  A105 c-Pr Me Et Me  A106 c-Pr Me Et Me  A107 c-Pr Me Et Me  A108 c-Pr Me Et Me  A109 c-Pr Me Et Me  A110 c-Pr Me Et Me  A111 c-Pr Me Et Me  A112 c-Pr Me Et Me  A113 c-Pr Me Et Me  A114 D1-108b-1 Me Et Me H D1-108b-4 Me Et Me H D1-108b-8 Me Et Me H D1-108b-16 Me Et Me H D1-108b-17 Me Et Me H D1-108b-18 Me Et Me H D1-108b-19 Me Et Me H CH₂Pr-c Me Et Me H CH₂Bu-c Me Et Me H CH₂Pen-c Me Et Me H CH₂-Hex-c Me Et Me H Me Me Et c-Pr H Me Me Et CH═CH₂ H Me Me Et CH═CHPr-n H Me Me Et CH═CHPh H Me Me Et C(O)Me H Me Me Et C(O)OMe H Me Me Et C(═NOMe)Me H Me Me Et OH H Me Me Et OMe H Me Me Et OCH₂CH₂OMe H Me Me Et OCH₂Ph H Me Me Et OCH₂(D1-34a) H Me Me Et OPh H Me Me Et O(D1-32b-1) H Me Me Et Me  A115 Me Me Et SMe H Me Me Et S(O)Me H Me Me Et S(O)₂Me H Me Me Et NHC(O)OBu-t H Me Me Et H H Me Me Et Br A1  Me Me Et Br A2  Me Me Et Br A3  Me Me Et Br A4  Me Me Et Br A5  Me Me Et Br A6  Me Me Et Br A7  Me Me Et Br A8  Me Me Et Br A9  Me Me Et Br A10 Me Me Et Br A11 Me Me Et Br A12 Me Me Et Br A13 Me Me Et Br A14 Me Me Et Br A15 Me Me Et Br A16 Me Me Et Br A17 Me Me Et Br A18 Me Me Et Br A19 Me Me Et Br A20 Me Me Et Br A21 Me Me Et Br A22 Me Me Et Br A23 Me Me Et Br A24 Me Me Et Br A25 Me Me Et Br A26 Me Me Et Br A27 Me Me Et Br A28 Me Me Et Br A29 Me Me Et Br A30 Me Me Et Br A31 Me Me Et Br A32 Me Me Et Br A33 Me Me Et Br A34 Me Me Et Br A35 Me Me Et Br A36 Me Me Et Br A37 Me Me Et Br A38 Me Me Et Br A39 Me Me Et Br A40 Me Me Et Br A41 Me Me Et Br A42 Me Me Et Br A43 Me Me Et Br A44 Me Me Et Br A45 Me Me Et Br A46 Me Me Et Br A47 Me Me Et Br A48 Me Me Et Br A49 Me Me Et Br A50 Me Me Et Br A51 Me Me Et Br A52 Me Me Et Br A53 Me Me Et Br A54 Me Me Et Br A55 Me Me Et Br A56 Me Me Et Br A57 Me Me Et Br A58 Me Me Et Br A59 Me Me Et Br A60 Me Me Et Br A61 Me Me Et Br A62 Me Me Et Br A63 Me Me Et Br A64 Me Me Et Br A65 Me Me Et Br A66 Me Me Et Br A67 Me Me Et Br A68 Me Me Et Br A69 Me Me Et Br A70 Me Me Et Br A71 Me Me Et Br A72 Me Me Et Br A73 Me Me Et Br A74 Me Me Et Br A75 Me Me Et Br A76 Me Me Et Br A77 Me Me Et Br A78 Me Me Et Br A79 Me Me Et Br A80 Me Me Et Br A81 Me Me Et Br A82 Me Me Et Br A83 Me Me Et Br A84 Me Me Et Br A85 Me Me Et Br A86 Me Me Et Br A87 Me Me Et Br A88 Me Me Et Br A89 Me Me Et Br A90 Me Me Et Br A91 Me Me Et Br A92 Me Me Et Br A93 Me Me Et Br A94 Me Me Et Br A95 Me Me Et Br A96 Me Me Et Br A97 Me Me Et Br A98 Me Me Et Br A99 Me Me Et Br  A100 Me Me Et Br  A101 Me Me Et Br  A102 Me Me Et Br  A103 Me Me Et Br  A104 Me Me Et Br  A105 Me Me Et Br  A106 Me Me Et Br  A107 Me Me Et Br  A108 Me Me Et Br  A109 Me Me Et Br  A110 Me Me Et Br  A111 Me Me Et Br  A112 Me Me Et Br  A113 Me Me Et Br  A114 Me Me Et Br  A115 Me Me Et Br  A116 Me Me n-Pr F H Me Me n-Pr Cl H Me Me n-Pr Br H Me Me n-Pr I H Me Me n-Pr CN H Me Me n-Pr NO₂ H CH═CH₂ Me n-Pr Me H c-Bu Me n-Pr Me H c-Pen Me n-Pr Me H c-Hex Me n-Pr Me H Ph Me n-Pr Me H CF₃ Me n-Pr Me H CH₂Cl Me n-Pr Me H CH₂OMe Me n-Pr Me H D1-32a Me n-Pr Me H Me Me n-Pr Me H Me Me n-Pr Me A1  Me Me n-Pr Me A2  Me Me n-Pr Me A3  Me Me n-Pr Me A4  Me Me n-Pr Me A5  Me Me n-Pr Me A6  Me Me n-Pr Me A7  Me Me n-Pr Me A8  Me Me n-Pr Me A9  Me Me n-Pr Me A10 Me Me n-Pr Me A11 Me Me n-Pr Me A12 Me Me n-Pr Me A13 Me Me n-Pr Me A14 Me Me n-Pr Me A15 Me Me n-Pr Me A16 Me Me n-Pr Me A17 Me Me n-Pr Me A18 Me Me n-Pr Me A19 Me Me n-Pr Me A20 Me Me n-Pr Me A21 Me Me n-Pr Me A22 Me Me n-Pr Me A23 Me Me n-Pr Me A24 Me Me n-Pr Me A25 Me Me n-Pr Me A26 Me Me n-Pr Me A27 Me Me n-Pr Me A28 Me Me n-Pr Me A29 Me Me n-Pr Me A30 Me Me n-Pr Me A31 Me Me n-Pr Me A32 Me Me n-Pr Me A33 Me Me n-Pr Me A34 Me Me n-Pr Me A35 Me Me n-Pr Me A36 Me Me n-Pr Me A37 Me Me n-Pr Me A38 Me Me n-Pr Me A39 Me Me n-Pr Me A40 Me Me n-Pr Me A41 Me Me n-Pr Me A42 Me Me n-Pr Me A43 Me Me n-Pr Me A44 Me Me n-Pr Me A45 Me Me n-Pr Me A46 Me Me n-Pr Me A47 Me Me n-Pr Me A48 Me Me n-Pr Me A49 Me Me n-Pr Me A50 Me Me n-Pr Me A51 Me Me n-Pr Me A52 Me Me n-Pr Me A53 Me Me n-Pr Me A54 Me Me n-Pr Me A55 Me Me n-Pr Me A56 Me Me n-Pr Me A57 Me Me n-Pr Me A58 Me Me n-Pr Me A59 Me Me n-Pr Me A60 Me Me n-Pr Me A61 Me Me n-Pr Me A62 Me Me n-Pr Me A63 Me Me n-Pr Me A64 Me Me n-Pr Me A65 Me Me n-Pr Me A66 Me Me n-Pr Me A67 Me Me n-Pr Me A68 Me Me n-Pr Me A69 Me Me n-Pr Me A70 Me Me n-Pr Me A71 Me Me n-Pr Me A72 Me Me n-Pr Me A73 Me Me n-Pr Me A74 Me Me n-Pr Me A75 Me Me n-Pr Me A76 Me Me n-Pr Me A77 Me Me n-Pr Me A78 Me Me n-Pr Me A79 Me Me n-Pr Me A80 Me Me n-Pr Me A81 Me Me n-Pr Me A82 Me Me n-Pr Me A83 Me Me n-Pr Me A84 Me Me n-Pr Me A85 Me Me n-Pr Me A86 Me Me n-Pr Me A87 Me Me n-Pr Me A88 Me Me n-Pr Me A89 Me Me n-Pr Me A90 Me Me n-Pr Me A91 Me Me n-Pr Me A92 Me Me n-Pr Me A93 Me Me n-Pr Me A94 Me Me n-Pr Me A95 Me Me n-Pr Me A96 Me Me n-Pr Me A97 Me Me n-Pr Me A98 Me Me n-Pr Me A99 Me Me n-Pr Me  A100 Me Me n-Pr Me  A101 Me Me n-Pr Me  A102 Me Me n-Pr Me  A103 Me Me n-Pr Me  A104 Me Me n-Pr Me  A105 Me Me n-Pr Me  A106 Me Me n-Pr Me  A107 Me Me n-Pr Me  A108 Me Me n-Pr Me  A109 Me Me n-Pr Me  A110 Me Me n-Pr Me  A111 Me Me n-Pr Me  A112 Me Me n-Pr Me  A113 Me Me n-Pr Me  A114 c-Pr Me n-Pr Me H c-Pr Me n-Pr Me A1  c-Pr Me n-Pr Me A2  c-Pr Me n-Pr Me A3  c-Pr Me n-Pr Me A4  c-Pr Me n-Pr Me A5  c-Pr Me n-Pr Me A6  c-Pr Me n-Pr Me A7  c-Pr Me n-Pr Me A8  c-Pr Me n-Pr Me A9  c-Pr Me n-Pr Me A10 c-Pr Me n-Pr Me A11 c-Pr Me n-Pr Me A12 c-Pr Me n-Pr Me A13 c-Pr Me n-Pr Me A14 c-Pr Me n-Pr Me A15 c-Pr Me n-Pr Me A16 c-Pr Me n-Pr Me A17 c-Pr Me n-Pr Me A18 c-Pr Me n-Pr Me A19 c-Pr Me n-Pr Me A20 c-Pr Me n-Pr Me A21 c-Pr Me n-Pr Me A22 c-Pr Me n-Pr Me A23 c-Pr Me n-Pr Me A24 c-Pr Me n-Pr Me A25 c-Pr Me n-Pr Me A26 c-Pr Me n-Pr Me A27 c-Pr Me n-Pr Me A28 c-Pr Me n-Pr Me A29 c-Pr Me n-Pr Me A30 c-Pr Me n-Pr Me A31 c-Pr Me n-Pr Me A32 c-Pr Me n-Pr Me A33 c-Pr Me n-Pr Me A34 c-Pr Me n-Pr Me A35 c-Pr Me n-Pr Me A36 c-Pr Me n-Pr Me A37 c-Pr Me n-Pr Me A38 c-Pr Me n-Pr Me A39 c-Pr Me n-Pr Me A40 c-Pr Me n-Pr Me A41 c-Pr Me n-Pr Me A42 c-Pr Me n-Pr Me A43 c-Pr Me n-Pr Me A44 c-Pr Me n-Pr Me A45 c-Pr Me n-Pr Me A46 c-Pr Me n-Pr Me A47 c-Pr Me n-Pr Me A48 c-Pr Me n-Pr Me A49 c-Pr Me n-Pr Me A50 c-Pr Me n-Pr Me A51 c-Pr Me n-Pr Me A52 c-Pr Me n-Pr Me A53 c-Pr Me n-Pr Me A54 c-Pr Me n-Pr Me A55 c-Pr Me n-Pr Me A56 c-Pr Me n-Pr Me A57 c-Pr Me n-Pr Me A58 c-Pr Me n-Pr Me A59 c-Pr Me n-Pr Me A60 c-Pr Me n-Pr Me A61 c-Pr Me n-Pr Me A62 c-Pr Me n-Pr Me A63 c-Pr Me n-Pr Me A64 c-Pr Me n-Pr Me A65 c-Pr Me n-Pr Me A66 c-Pr Me n-Pr Me A67 c-Pr Me n-Pr Me A68 c-Pr Me n-Pr Me A69 c-Pr Me n-Pr Me A70 c-Pr Me n-Pr Me A71 c-Pr Me n-Pr Me A72 c-Pr Me n-Pr Me A73 c-Pr Me n-Pr Me A74 c-Pr Me n-Pr Me A75 c-Pr Me n-Pr Me A76 c-Pr Me n-Pr Me A77 c-Pr Me n-Pr Me A78 c-Pr Me n-Pr Me A79 c-Pr Me n-Pr Me A80 c-Pr Me n-Pr Me A81 c-Pr Me n-Pr Me A82 c-Pr Me n-Pr Me A83 c-Pr Me n-Pr Me A84 c-Pr Me n-Pr Me A85 c-Pr Me n-Pr Me A86 c-Pr Me n-Pr Me A87 c-Pr Me n-Pr Me A88 c-Pr Me n-Pr Me A89 c-Pr Me n-Pr Me A90 c-Pr Me n-Pr Me A91 c-Pr Me n-Pr Me A92 c-Pr Me n-Pr Me A93 c-Pr Me n-Pr Me A94 c-Pr Me n-Pr Me A95 c-Pr Me n-Pr Me A96 c-Pr Me n-Pr Me A97 c-Pr Me n-Pr Me A98 c-Pr Me n-Pr Me A99 c-Pr Me n-Pr Me  A100 c-Pr Me n-Pr Me  A101 c-Pr Me n-Pr Me  A102 c-Pr Me n-Pr Me  A103 c-Pr Me n-Pr Me  A104 c-Pr Me n-Pr Me  A105 c-Pr Me n-Pr Me  A106 c-Pr Me n-Pr Me  A107 c-Pr Me n-Pr Me  A108 c-Pr Me n-Pr Me  A109 c-Pr Me n-Pr Me  A110 c-Pr Me n-Pr Me  A111 c-Pr Me n-Pr Me  A112 c-Pr Me n-Pr Me  A113 c-Pr Me n-Pr Me  A114 D1-108b-1 Me n-Pr Me H D1-108b-4 Me n-Pr Me H D1-108b-8 Me n-Pr Me H D1-108b-16 Me n-Pr Me H D1-108b-17 Me n-Pr Me H D1-108b-18 Me n-Pr Me H D1-108b-19 Me n-Pr Me H CH₂Pr-c Me n-Pr Me H CH₂Bu-c Me n-Pr Me H CH₂Pen-c Me n-Pr Me H CH₂-Hex-c Me n-Pr Me H Me Me n-Pr c-Pr H Me Me n-Pr CH═CH₂ H Me Me n-Pr CH═CHPr-n H Me Me n-Pr CH═CHPh H Me Me n-Pr C(O)Me H Me Me n-Pr C(O)OMe H Me Me n-Pr C(═NOMe)Me H Me Me n-Pr OH H Me Me n-Pr OMe H Me Me n-Pr OCH₂CH₂OMe H Me Me n-Pr OCH₂Ph H Me Me n-Pr OCH₂(D1-34a) H Me Me n-Pr OPh H Me Me n-Pr O(D1-32b-1) H Me Me n-Pr Me  A115 Me Me n-Pr SMe H Me Me n-Pr S(O)Me H Me Me n-Pr S(O)₂Me H Me Me n-Pr NHC(O)OBu-t H Me Me n-Pr H H Me Me n-Pr Br A1  Me Me n-Pr Br A2  Me Me n-Pr Br A3  Me Me n-Pr Br A4  Me Me n-Pr Br A5  Me Me n-Pr Br A6  Me Me n-Pr Br A7  Me Me n-Pr Br A8  Me Me n-Pr Br A9  Me Me n-Pr Br A10 Me Me n-Pr Br A11 Me Me n-Pr Br A12 Me Me n-Pr Br A13 Me Me n-Pr Br A14 Me Me n-Pr Br A15 Me Me n-Pr Br A16 Me Me n-Pr Br A17 Me Me n-Pr Br A18 Me Me n-Pr Br A19 Me Me n-Pr Br A20 Me Me n-Pr Br A21 Me Me n-Pr Br A22 Me Me n-Pr Br A23 Me Me n-Pr Br A24 Me Me n-Pr Br A25 Me Me n-Pr Br A26 Me Me n-Pr Br A27 Me Me n-Pr Br A28 Me Me n-Pr Br A29 Me Me n-Pr Br A30 Me Me n-Pr Br A31 Me Me n-Pr Br A32 Me Me n-Pr Br A33 Me Me n-Pr Br A34 Me Me n-Pr Br A35 Me Me n-Pr Br A36 Me Me n-Pr Br A37 Me Me n-Pr Br A38 Me Me n-Pr Br A39 Me Me n-Pr Br A40 Me Me n-Pr Br A41 Me Me n-Pr Br A42 Me Me n-Pr Br A43 Me Me n-Pr Br A44 Me Me n-Pr Br A45 Me Me n-Pr Br A46 Me Me n-Pr Br A47 Me Me n-Pr Br A48 Me Me n-Pr Br A49 Me Me n-Pr Br A50 Me Me n-Pr Br A51 Me Me n-Pr Br A52 Me Me n-Pr Br A53 Me Me n-Pr Br A54 Me Me n-Pr Br A55 Me Me n-Pr Br A56 Me Me n-Pr Br A57 Me Me n-Pr Br A58 Me Me n-Pr Br A59 Me Me n-Pr Br A60 Me Me n-Pr Br A61 Me Me n-Pr Br A62 Me Me n-Pr Br A63 Me Me n-Pr Br A64 Me Me n-Pr Br A65 Me Me n-Pr Br A66 Me Me n-Pr Br A67 Me Me n-Pr Br A68 Me Me n-Pr Br A69 Me Me n-Pr Br A70 Me Me n-Pr Br A71 Me Me n-Pr Br A72 Me Me n-Pr Br A73 Me Me n-Pr Br A74 Me Me n-Pr Br A75 Me Me n-Pr Br A76 Me Me n-Pr Br A77 Me Me n-Pr Br A78 Me Me n-Pr Br A79 Me Me n-Pr Br A80 Me Me n-Pr Br A81 Me Me n-Pr Br A82 Me Me n-Pr Br A83 Me Me n-Pr Br A84 Me Me n-Pr Br A85 Me Me n-Pr Br A86 Me Me n-Pr Br A87 Me Me n-Pr Br A88 Me Me n-Pr Br A89 Me Me n-Pr Br A90 Me Me n-Pr Br A91 Me Me n-Pr Br A92 Me Me n-Pr Br A93 Me Me n-Pr Br A94 Me Me n-Pr Br A95 Me Me n-Pr Br A96 Me Me n-Pr Br A97 Me Me n-Pr Br A98 Me Me n-Pr Br A99 Me Me n-Pr Br  A100 Me Me n-Pr Br  A101 Me Me n-Pr Br  A102 Me Me n-Pr Br  A103 Me Me n-Pr Br  A104 Me Me n-Pr Br  A105 Me Me n-Pr Br  A106 Me Me n-Pr Br  A107 Me Me n-Pr Br  A108 Me Me n-Pr Br  A109 Me Me n-Pr Br  A110 Me Me n-Pr Br  A111 Me Me n-Pr Br  A112 Me Me n-Pr Br  A113 Me Me n-Pr Br  A114 Me Me n-Pr Br  A115 Me Et Et Br  A116 H Et Et F H H Et Et Cl H H Et Et Br H H Et Et I H H Et Et CN H H Et Et NO₂ H H Et Et Me H H Et Et Me A1  H Et Et Me A2  H Et Et Me A3  H Et Et Me A4  H Et Et Me A5  H Et Et Me A6  H Et Et Me A7  H Et Et Me A8  H Et Et Me A9  H Et Et Me A10 H Et Et Me A11 H Et Et Me A12 H Et Et Me A13 H Et Et Me A14 H Et Et Me A15 H Et Et Me A16 H Et Et Me A17 H Et Et Me A18 H Et Et Me A19 H Et Et Me A20 H Et Et Me A21 H Et Et Me A22 H Et Et Me A23 H Et Et Me A24 H Et Et Me A25 H Et Et Me A26 H Et Et Me A27 H Et Et Me A28 H Et Et Me A29 H Et Et Me A30 H Et Et Me A31 H Et Et Me A32 H Et Et Me A33 H Et Et Me A34 H Et Et Me A35 H Et Et Me A36 H Et Et Me A37 H Et Et Me A38 H Et Et Me A39 H Et Et Me A40 H Et Et Me A41 H Et Et Me A42 H Et Et Me A43 H Et Et Me A44 H Et Et Me A45 H Et Et Me A46 H Et Et Me A47 H Et Et Me A48 H Et Et Me A49 H Et Et Me A50 H Et Et Me A51 H Et Et Me A52 H Et Et Me A53 H Et Et Me A54 H Et Et Me A55 H Et Et Me A56 H Et Et Me A57 H Et Et Me A58 H Et Et Me A59 H Et Et Me A60 H Et Et Me A61 H Et Et Me A62 H Et Et Me A63 H Et Et Me A64 H Et Et Me A65 H Et Et Me A66 H Et Et Me A67 H Et Et Me A68 H Et Et Me A69 H Et Et Me A70 H Et Et Me A71 H Et Et Me A72 H Et Et Me A73 H Et Et Me A74 H Et Et Me A75 H Et Et Me A76 H Et Et Me A77 H Et Et Me A78 H Et Et Me A79 H Et Et Me A80 H Et Et Me A81 H Et Et Me A82 H Et Et Me A83 H Et Et Me A84 H Et Et Me A85 H Et Et Me A86 H Et Et Me A87 H Et Et Me A88 H Et Et Me A89 H Et Et Me A90 H Et Et Me A91 H Et Et Me A92 H Et Et Me A93 H Et Et Me A94 H Et Et Me A95 H Et Et Me A96 H Et Et Me A97 H Et Et Me A98 H Et Et Me A99 H Et Et Me  A100 H Et Et Me  A101 H Et Et Me  A102 H Et Et Me  A103 H Et Et Me  A104 H Et Et Me  A105 H Et Et Me  A106 H Et Et c-Pr H H Et Et CH═CH₂ H H Et Et CH═CHPr-n H H Et Et CH═CHPh H H Et Et C(O)Me H H Et Et C(O)OMe H H Et Et C(═NOMe)Me H H Et Et OH H H Et Et OMe H H Et Et OCH₂CH₂OMe H H Et Et OCH₂Ph H H Et Et OCH₂(D1-34a) H H Et Et OPh H H Et Et O(D1-32b-1) H H Et Et Me H H Et Et SMe H H Et Et S(O)Me H H Et Et S(O)₂Me H H Et Et NHC(O)OBu-t H Me Et Et Me A116 Me Me n-Pr Me A116 CH₂OMe Me Me Me A1  CH₂OMe Me Me Me A13 CH₂OMe Me Me Me A14 CH₂OMe Me Me Me A15 CH₂OMe Me Me Me A16 CH₂OMe Me Me Me A20 CH₂OMe Me Me Me A23 CH₂OMe Me Me Me A24 CH₂OMe Me Me Me A25 CH₂OMe Me Me Me A26 CH₂OMe Me Me Me A27 CH₂OMe Me Me Me A28 CH₂OMe Me Me Me A29 CH₂OMe Me Me Me A34 CH₂OMe Me Me Me A35 CH₂OMe Me Me Me A36 CH₂OMe Me Me Me A37 CH₂OMe Me Me Me A42 CH₂OMe Me Me Me A58 CH₂OMe Me Me Me A63 CH₂OMe Me Me Me A64 CH₂OMe Me Me Me A65 CH₂OMe Me Me Me A67 CH₂OMe Me Me Me A69 CH₂OMe Me Me Me A72 CH₂OMe Me Me Me A73 CH₂OMe Me Me Me A74 CH₂OMe Me Me Me A75 CH₂OMe Me Me Me A76 CH₂OMe Me Me Me A77 CH₂OMe Me Me Me A81 CH₂OMe Me Me Me A83 CH₂OMe Me Me Me A88 CH₂OMe Me Me Me A91 CH₂OMe Me Me Me A97 CH₂OMe Me Me Me A98 CH₂OMe Me Me Me  A102 D1-108b-1 Me Me Me A1  D1-108b-1 Me Me Me A13 D1-108b-1 Me Me Me A14 D1-108b-1 Me Me Me A15 D1-108b-1 Me Me Me A16 D1-108b-1 Me Me Me A20 D1-108b-1 Me Me Me A23 D1-108b-1 Me Me Me A24 D1-108b-1 Me Me Me A25 D1-108b-1 Me Me Me A26 D1-108b-1 Me Me Me A27 D1-108b-1 Me Me Me A28 D1-108b-1 Me Me Me A29 D1-108b-1 Me Me Me A34 D1-108b-1 Me Me Me A35 D1-108b-1 Me Me Me A36 D1-108b-1 Me Me Me A37 D1-108b-1 Me Me Me A42 D1-108b-1 Me Me Me A58 D1-108b-1 Me Me Me A63 D1-108b-1 Me Me Me A64 D1-108b-1 Me Me Me A65 D1-108b-1 Me Me Me A67 D1-108b-1 Me Me Me A69 D1-108b-1 Me Me Me A72 D1-108b-1 Me Me Me A73 D1-108b-1 Me Me Me A74 D1-108b-1 Me Me Me A75 D1-108b-1 Me Me Me A76 D1-108b-1 Me Me Me A77 D1-108b-1 Me Me Me A81 D1-108b-1 Me Me Me A83 D1-108b-1 Me Me Me A88 D1-108b-1 Me Me Me A91 D1-108b-1 Me Me Me A97 D1-108b-1 Me Me Me A98 D1-108b-1 Me Me Me  A102 D1-108b-8 Me Me Me A1  D1-108b-8 Me Me Me A13 D1-108b-8 Me Me Me A14 D1-108b-8 Me Me Me A15 D1-108b-8 Me Me Me A16 D1-108b-8 Me Me Me A20 D1-108b-8 Me Me Me A23 D1-108b-8 Me Me Me A24 D1-108b-8 Me Me Me A25 D1-108b-8 Me Me Me A26 D1-108b-8 Me Me Me A27 D1-108b-8 Me Me Me A28 D1-108b-8 Me Me Me A29 D1-108b-8 Me Me Me A34 D1-108b-8 Me Me Me A35 D1-108b-8 Me Me Me A36 D1-108b-8 Me Me Me A37 D1-108b-8 Me Me Me A42 D1-108b-8 Me Me Me A58 D1-108b-8 Me Me Me A63 D1-108b-8 Me Me Me A64 D1-108b-8 Me Me Me A65 D1-108b-8 Me Me Me A67 D1-108b-8 Me Me Me A69 D1-108b-8 Me Me Me A72 D1-108b-8 Me Me Me A73 D1-108b-8 Me Me Me A74 D1-108b-8 Me Me Me A75 D1-108b-8 Me Me Me A76 D1-108b-8 Me Me Me A77 D1-108b-8 Me Me Me A81 D1-108b-8 Me Me Me A83 D1-108b-8 Me Me Me A88 D1-108b-8 Me Me Me A91 D1-108b-8 Me Me Me A97 D1-108b-8 Me Me Me A98 D1-108b-8 Me Me Me  A102 Me Me Me CN A1  Me Me Me CN A13 Me Me Me CN A14 Me Me Me CN A15 Me Me Me CN A16 Me Me Me CN A20 Me Me Me CN A23 Me Me Me CN A24 Me Me Me CN A25 Me Me Me CN A26 Me Me Me CN A27 Me Me Me CN A28 Me Me Me CN A29 Me Me Me CN A34 Me Me Me CN A35 Me Me Me CN A36 Me Me Me CN A37 Me Me Me CN A42 Me Me Me CN A58 Me Me Me CN A63 Me Me Me CN A64 Me Me Me CN A65 Me Me Me CN A67 Me Me Me CN A69 Me Me Me CN A72 Me Me Me CN A73 Me Me Me CN A74 Me Me Me CN A75 D1-108b-8 Me Me CN A76 D1-108b-8 Me Me CN A77 D1-108b-8 Me Me CN A81 D1-108b-8 Me Me CN A83 D1-108b-8 Me Me CN A88 D1-108b-8 Me Me CN A91 D1-108b-8 Me Me CN A97 D1-108b-8 Me Me CN A98 D1-108b-8 Me Me CN  A102 Me Me Me c-Pr A1  Me Me Me c-Pr A13 Me Me Me c-Pr A14 Me Me Me c-Pr A15 Me Me Me c-Pr A16 Me Me Me c-Pr A20 Me Me Me c-Pr A23 Me Me Me c-Pr A24 Me Me Me c-Pr A25 Me Me Me c-Pr A26 Me Me Me c-Pr A27 Me Me Me c-Pr A28 Me Me Me c-Pr A29 Me Me Me c-Pr A34 Me Me Me c-Pr A35 Me Me Me c-Pr A36 Me Me Me c-Pr A37 Me Me Me c-Pr A42 Me Me Me c-Pr A58 Me Me Me c-Pr A63 Me Me Me c-Pr A64 Me Me Me c-Pr A65 Me Me Me c-Pr A67 Me Me Me c-Pr A69 Me Me Me c-Pr A72 Me Me Me c-Pr A73 Me Me Me c-Pr A74 Me Me Me c-Pr A75 Me Me Me c-Pr A76 Me Me Me c-Pr A77 Me Me Me c-Pr A81 Me Me Me c-Pr A83 Me Me Me c-Pr A88 Me Me Me c-Pr A91 Me Me Me c-Pr A97 Me Me Me c-Pr A98 Me Me Me c-Pr  A102 Me Me Me CH═CHPh A1  Me Me Me CH═CHPh A13 Me Me Me CH═CHPh A14 Me Me Me CH═CHPh A15 Me Me Me CH═CHPh A16 Me Me Me CH═CHPh A20 Me Me Me CH═CHPh A23 Me Me Me CH═CHPh A24 Me Me Me CH═CHPh A25 Me Me Me CH═CHPh A26 Me Me Me CH═CHPh A27 Me Me Me CH═CHPh A28 Me Me Me CH═CHPh A29 Me Me Me CH═CHPh A34 Me Me Me CH═CHPh A35 Me Me Me CH═CHPh A36 Me Me Me CH═CHPh A37 Me Me Me CH═CHPh A42 Me Me Me CH═CHPh A58 Me Me Me CH═CHPh A63 Me Me Me CH═CHPh A64 Me Me Me CH═CHPh A65 Me Me Me CH═CHPh A67 Me Me Me CH═CHPh A69 Me Me Me CH═CHPh A72 Me Me Me CH═CHPh A73 Me Me Me CH═CHPh A74 Me Me Me CH═CHPh A75 Me Me Me CH═CHPh A76 Me Me Me CH═CHPh A77 Me Me Me CH═CHPh A81 Me Me Me CH═CHPh A83 Me Me Me CH═CHPh A88 Me Me Me CH═CHPh A91 Me Me Me CH═CHPh A97 Me Me Me CH═CHPh A98 Me Me Me CH═CHPh  A102 Me Me Me C(O)OMe A1  Me Me Me C(O)OMe A13 Me Me Me C(O)OMe A14 Me Me Me C(O)OMe A15 Me Me Me C(O)OMe A16 Me Me Me C(O)OMe A20 Me Me Me C(O)OMe A23 Me Me Me C(O)OMe A24 Me Me Me C(O)OMe A25 Me Me Me C(O)OMe A26 Me Me Me C(O)OMe A27 Me Me Me C(O)OMe A28 Me Me Me C(O)OMe A29 Me Me Me C(O)OMe A34 Me Me Me C(O)OMe A35 Me Me Me C(O)OMe A36 Me Me Me C(O)OMe A37 Me Me Me C(O)OMe A42 Me Me Me C(O)OMe A58 Me Me Me C(O)OMe A63 Me Me Me C(O)OMe A64 Me Me Me C(O)OMe A65 Me Me Me C(O)OMe A67 Me Me Me C(O)OMe A69 Me Me Me C(O)OMe A72 Me Me Me C(O)OMe A73 Me Me Me C(O)OMe A74 Me Me Me C(O)OMe A75 Me Me Me C(O)OMe A76 Me Me Me C(O)OMe A77 Me Me Me C(O)OMe A81 Me Me Me C(O)OMe A83 Me Me Me C(O)OMe A88 Me Me Me C(O)OMe A91 Me Me Me C(O)OMe A97 Me Me Me C(O)OMe A98 Me Me Me OH A1  Me Me Me OH A13 Me Me Me OH A14 Me Me Me OH A15 Me Me Me OH A16 Me Me Me OH A20 Me Me Me OH A23 Me Me Me OH A24 Me Me Me OH A25 Me Me Me OH A26 Me Me Me OH A27 Me Me Me OH A28 Me Me Me OH A29 Me Me Me OH A34 Me Me Me OH A35 Me Me Me OH A36 Me Me Me OH A37 Me Me Me OH A42 Me Me Me OH A58 Me Me Me OH A63 Me Me Me OH A64 Me Me Me OH A65 Me Me Me OH A67 Me Me Me OH A69 Me Me Me OH A72 Me Me Me OH A73 Me Me Me OH A74 Me Me Me OH A75 Me Me Me OH A76 Me Me Me OH A77 Me Me Me OH A81 Me Me Me OH A83 Me Me Me OH A88 Me Me Me OH A91 Me Me Me OH A97 Me Me Me OH A98 Me Me Me OH  A102 Me Me Me OCH₂OMe A1  Me Me Me OCH₂OMe A13 Me Me Me OCH₂OMe A14 Me Me Me OCH₂OMe A15 Me Me Me OCH₂OMe A16 Me Me Me OCH₂OMe A20 Me Me Me OCH₂OMe A23 Me Me Me OCH₂OMe A24 Me Me Me OCH₂OMe A25 Me Me Me OCH₂OMe A26 Me Me Me OCH₂OMe A27 Me Me Me OCH₂OMe A28 Me Me Me OCH₂OMe A29 Me Me Me OCH₂OMe A34 Me Me Me OCH₂OMe A35 Me Me Me OCH₂OMe A36 Me Me Me OCH₂OMe A37 Me Me Me OCH₂OMe A42 Me Me Me OCH₂OMe A58 Me Me Me OCH₂OMe A63 Me Me Me OCH₂OMe A64 Me Me Me OCH₂OMe A65 Me Me Me OCH₂OMe A67 Me Me Me OCH₂OMe A69 Me Me Me OCH₂OMe A72 Me Me Me OCH₂OMe A73 Me Me Me OCH₂OMe A74 Me Me Me OCH₂OMe A75 Me Me Me OCH₂OMe A76 Me Me Me OCH₂OMe A77 Me Me Me OCH₂OMe A81 Me Me Me OCH₂OMe A83 Me Me Me OCH₂OMe A88 Me Me Me OCH₂OMe A91 Me Me Me OCH₂OMe A97 Me Me Me OCH₂OMe A98 Me Me Me OCH₂OMe  A102 Me Me Me OCH₂(D1-34a) A1  Me Me Me OCH₂(D1-34a) A13 Me Me Me OCH₂(D1-34a) A14 Me Me Me OCH₂(D1-34a) A15 Me Me Me OCH₂(D1-34a) A16 Me Me Me OCH₂(D1-34a) A20 Me Me Me OCH₂(D1-34a) A23 Me Me Me OCH₂(D1-34a) A24 Me Me Me OCH₂(D1-34a) A25 Me Me Me OCH₂(D1-34a) A26 Me Me Me OCH₂(D1-34a) A27 Me Me Me OCH₂(D1-34a) A28 Me Me Me OCH₂(D1-34a) A29 Me Me Me OCH₂(D1-34a) A34 Me Me Me OCH₂(D1-34a) A35 Me Me Me OCH₂(D1-34a) A36 Me Me Me OCH₂(D1-34a) A37 Me Me Me OCH₂(D1-34a) A42 Me Me Me OCH₂(D1-34a) A58 Me Me Me OCH₂(D1-34a) A63 Me Me Me OCH₂(D1-34a) A64 Me Me Me OCH₂(D1-34a) A65 Me Me Me OCH₂(D1-34a) A67 Me Me Me OCH₂(D1-34a) A69 Me Me Me OCH₂(D1-34a) A72 Me Me Me OCH₂(D1-34a) A73 Me Me Me OCH₂(D1-34a) A74 Me Me Me OCH₂(D1-34a) A75 Me Me Me OCH₂(D1-34a) A76 Me Me Me OCH₂(D1-34a) A77 Me Me Me OCH₂(D1-34a) A81 Me Me Me OCH₂(D1-34a) A83 Me Me Me OCH₂(D1-34a) A88 Me Me Me OCH₂(D1-34a) A91 Me Me Me OCH₂(D1-34a) A97 Me Me Me OCH₂(D1-34a) A98 Me Me Me OCH₂(D1-34a)  A102 Me Me Me O(D1-32b-1) A1  Me Me Me O(D1-32b-1) A13 Me Me Me O(D1-32b-1) A14 Me Me Me O(D1-32b-1) A15 Me Me Me O(D1-32b-1) A16 Me Me Me O(D1-32b-1) A20 Me Me Me O(D1-32b-1) A23 Me Me Me O(D1-32b-1) A24 Me Me Me O(D1-32b-1) A25 Me Me Me O(D1-32b-1) A26 Me Me Me O(D1-32b-1) A27 Me Me Me O(D1-32b-1) A28 Me Me Me O(D1-32b-1) A29 Me Me Me O(D1-32b-1) A34 Me Me Me O(D1-32b-1) A35 Me Me Me O(D1-32b-1) A36 Me Me Me O(D1-32b-1) A37 Me Me Me O(D1-32b-1) A42 Me Me Me O(D1-32b-1) A58 Me Me Me O(D1-32b-1) A63 Me Me Me O(D1-32b-1) A64 Me Me Me O(D1-32b-1) A65 Me Me Me O(D1-32b-1) A67 Me Me Me O(D1-32b-1) A69 Me Me Me O(D1-32b-1) A72 Me Me Me O(D1-32b-1) A73 Me Me Me O(D1-32b-1) A74 Me Me Me O(D1-32b-1) A75 Me Me Me O(D1-32b-1) A76 Me Me Me O(D1-32b-1) A77 Me Me Me O(D1-32b-1) A81 Me Me Me O(D1-32b-1) A83 Me Me Me O(D1-32b-1) A88 Me Me Me O(D1-32b-1) A91 Me Me Me O(D1-32b-1) A97 Me Me Me O(D1-32b-1) A98 Me Me Me O(D1-32b-1)  A102 Me Me Me NHC(O)OBu-t A1  Me Me Me NHC(O)OBu-t A13 Me Me Me NHC(O)OBu-t A14 Me Me Me NHC(O)OBu-t A15 Me Me Me NHC(O)OBu-t A16 Me Me Me NHC(O)OBu-t A20 Me Me Me NHC(O)OBu-t A23 Me Me Me NHC(O)OBu-t A24 Me Me Me NHC(O)OBu-t A25 Me Me Me NHC(O)OBu-t A26 Me Me Me NHC(O)OBu-t A27 Me Me Me NHC(O)OBu-t A28 Me Me Me NHC(O)OBu-t A29 Me Me Me NHC(O)OBu-t A34 Me Me Me NHC(O)OBu-t A35 Me Me Me NHC(O)OBu-t A36 Me Me Me NHC(O)OBu-t A37 Me Me Me NHC(O)OBu-t A42 Me Me Me NHC(O)OBu-t A58 Me Me Me NHC(O)OBu-t A63 Me Me Me NHC(O)OBu-t A64 Me Me Me NHC(O)OBu-t A65 Me Me Me NHC(O)OBu-t A67 Me Me Me NHC(O)OBu-t A69 Me Me Me NHC(O)OBu-t A72 Me Me Me NHC(O)OBu-t A73 Me Me Me NHC(O)OBu-t A74 Me Me Me NHC(O)OBu-t A75 Me Me Me NHC(O)OBu-t A76 Me Me Me NHC(O)OBu-t A77 Me Me Me NHC(O)OBu-t A81 Me Me Me NHC(O)OBu-t A83 Me Me Me NHC(O)OBu-t A88 Me Me Me NHC(O)OBu-t A91 Me Me Me NHC(O)OBu-t A97 Me Me Me NHC(O)OBu-t A98 Me Me Me NHC(O)OBu-t  A102

TABLE 2

R⁶ Z^(a) Z^(c) Z^(e) A R⁶ Z^(a) Z^(c) Z^(e) A Me Me Me C≡CMe H Me Me Et C≡CMe H Me Me Me C≡CMe A39 Me Me Et C≡CMe A39 Me Me Me C≡CMe A40 Me Me Et C≡CMe A40 Me Me Me C≡CMe A41 Me Me Et C≡CMe A41 c-Pr Me Me C≡CMe H c-Pr Me Et C≡CMe H c-Pr Me Me C≡CMe A39 c-Pr Me Et C≡CMe A39 c-Pr Me Me C≡CMe A40 c-Pr Me Et C≡CMe A40 c-Pr Me Me C≡CMe A41 c-Pr Me Et C≡CMe A41 c-Bu Me Me C≡CMe H c-Bu Me Et C≡CMe H c-Bu Me Me C≡CMe A39 c-Bu Me Et C≡CMe A39 c-Bu Me Me C≡CMe A40 c-Bu Me Et C≡CMe A40 c-Bu Me Me C≡CMe A41 c-Bu Me Et C≡CMe A41 c-Pen Me Me C≡CMe H c-Pen Me Et C≡CMe H c-Pen Me Me C≡CMe A39 c-Pen Me Et C≡CMe A39 c-Pen Me Me C≡CMe A40 c-Pen Me Et C≡CMe A40 c-Pen Me Me C≡CMe A41 c-Pen Me Et C≡CMe A41 c-Hex Me Me C≡CMe H c-Hex Me Et C≡CMe H c-Hex Me Me C≡CMe A39 c-Hex Me Et C≡CMe A39 c-Hex Me Me C≡CMe A40 c-Hex Me Et C≡CMe A40 c-Hex Me Me C≡CMe A41 c-Hex Me Et C≡CMe A41 Me Me Me C≡CSi(Me)₃ H Me Me Et C≡CSi(Me)₃ H Me Me Me C≡CSi(Me)₃ A39 Me Me Et C≡CSi(Me)₃ A39 Me Me Me C≡CSi(Me)₃ A40 Me Me Et C≡CSi(Me)₃ A40 Me Me Me C≡CSi(Me)₃ A41 Me Me Et C≡CSi(Me)₃ A41 c-Pr Me Me C≡CSi(Me)₃ H c-Pr Me Et C≡CSi(Me)₃ H c-Pr Me Me C≡CSi(Me)₃ A39 c-Pr Me Et C≡CSi(Me)₃ A39 c-Pr Me Me C≡CSi(Me)₃ A40 c-Pr Me Et C≡CSi(Me)₃ A40 c-Pr Me Me C≡CSi(Me)₃ A41 c-Pr Me Et C≡CSi(Me)₃ A41 c-Bu Me Me C≡CSi(Me)₃ H c-Bu Me Et C≡CSi(Me)₃ H c-Bu Me Me C≡CSi(Me)₃ A39 c-Bu Me Et C≡CSi(Me)₃ A39 c-Bu Me Me C≡CSi(Me)₃ A40 c-Bu Me Et C≡CSi(Me)₃ A40 c-Bu Me Me C≡CSi(Me)₃ A41 c-Bu Me Et C≡CSi(Me)₃ A41 c-Pen Me Me C≡CSi(Me)₃ H c-Pen Me Et C≡CSi(Me)₃ H c-Pen Me Me C≡CSi(Me)₃ A39 c-Pen Me Et C≡CSi(Me)₃ A39 c-Pen Me Me C≡CSi(Me)₃ A40 c-Pen Me Et C≡CSi(Me)₃ A40 c-Pen Me Me C≡CSi(Me)₃ A41 c-Pen Me Et C≡CSi(Me)₃ A41 c-Hex Me Me C≡CSi(Me)₃ H c-Hex Me Et C≡CSi(Me)₃ H c-Hex Me Me C≡CSi(Me)₃ A39 c-Hex Me Et C≡CSi(Me)₃ A39 c-Hex Me Me C≡CSi(Me)₃ A40 c-Hex Me Et C≡CSi(Me)₃ A40 c-Hex Me Me C≡CSi(Me)₃ A41 c-Hex Me Et C≡CSi(Me)₃ A41 Me Me Me C≡CPr-c H Me Me Et C≡CPr-c H Me Me Me C≡CPr-c A39 Me Me Et C≡CPr-c A39 Me Me Me C≡CPr-c A40 Me Me Et C≡CPr-c A40 Me Me Me C≡CPr-c A41 Me Me Et C≡CPr-c A41 c-Pr Me Me C≡CPr-c H c-Pr Me Et C≡CPr-c H c-Pr Me Me C≡CPr-c A39 c-Pr Me Et C≡CPr-c A39 c-Pr Me Me C≡CPr-c A40 c-Pr Me Et C≡CPr-c A40 c-Pr Me Me C≡CPr-c A41 c-Pr Me Et C≡CPr-c A41 c-Bu Me Me C≡CPr-c H c-Bu Me Et C≡CPr-c H c-Bu Me Me C≡CPr-c A39 c-Bu Me Et C≡CPr-c A39 c-Bu Me Me C≡CPr-c A40 c-Bu Me Et C≡CPr-c A40 c-Bu Me Me C≡CPr-c A41 c-Bu Me Et C≡CPr-c A41 c-Pen Me Me C≡CPr-c H c-Pen Me Et C≡CPr-c H c-Pen Me Me C≡CPr-c A39 c-Pen Me Et C≡CPr-c A39 c-Pen Me Me C≡CPr-c A40 c-Pen Me Et C≡CPr-c A40 c-Pen Me Me C≡CPr-c A41 c-Pen Me Et C≡CPr-c A41 c-Hex Me Me C≡CPr-c H c-Hex Me Et C≡CPr-c H c-Hex Me Me C≡CPr-c A39 c-Hex Me Et C≡CPr-c A39 c-Hex Me Me C≡CPr-c A40 c-Hex Me Et C≡CPr-c A40 c-Hex Me Me C≡CPr-c A41 c-Hex Me Et C≡CPr-c A41 Me Me Me C≡CC(Me)₂OH H Me Me Et C≡CC(Me)₂OH H Me Me Me C≡CC(Me)₂OH A39 Me Me Et C≡CC(Me)₂OH A39 Me Me Me C≡CC(Me)₂OH A40 Me Me Et C≡CC(Me)₂OH A40 Me Me Me C≡CC(Me)₂OH A41 Me Me Et C≡CC(Me)₂OH A41 Me Me Me C≡CCH₂OH H Me Me Et C≡CCH₂OH H Me Me Me C≡CCH₂OH A39 Me Me Et C≡CCH₂OH A39 Me Me Me C≡CCH₂OH A40 Me Me Et C≡CCH₂OH A40 Me Me Me C≡CCH₂OH A41 Me Me Et C≡CCH₂OH A41 Me Me Me Ph H Me Me Et Ph H Me Me Me Ph Me Me Me Et Ph Me Me Me Me Ph A11 Me Me Et Ph A11 Me Me Me Ph A34 Me Me Et Ph A34 Me Me Me Ph A35 Me Me Et Ph A35 Me Me Me Ph A37 Me Me Et Ph A37 Me Me Me Ph A39 Me Me Et Ph A39 Me Me Me Ph A40 Me Me Et Ph A40 Me Me Me Ph A41 Me Me Et Ph A41 Me Me Me Ph A73 Me Me Et Ph A73 Me Me Me Ph A75 Me Me Et Ph A75 Me Me Me Ph A83 Me Me Et Ph A83 Me Me Me Ph A84 Me Me Et Ph A84 Me Me Me Ph A85 Me Me Et Ph A85 Me Me Me Ph A91 Me Me Et Ph A91 Me Me Me D1-108b-1 H Me Me Et D1-108b-1 H Me Me Me D1-108b-1 Me Me Me Et D1-108b-1 Me Me Me Me D1-108b-1 A11 Me Me Et D1-108b-1 A11 Me Me Me D1-108b-1 A34 Me Me Et D1-108b-1 A34 Me Me Me D1-108b-1 A35 Me Me Et D1-108b-1 A35 Me Me Me D1-108b-1 A37 Me Me Et D1-108b-1 A37 Me Me Me D1-108b-1 A39 Me Me Et D1-108b-1 A39 Me Me Me D1-108b-1 A40 Me Me Et D1-108b-1 A40 Me Me Me D1-108b-1 A41 Me Me Et D1-108b-1 A41 Me Me Me D1-108b-1 A73 Me Me Et D1-108b-1 A73 Me Me Me D1-108b-1 A75 Me Me Et D1-108b-1 A75 Me Me Me D1-108b-1 A83 Me Me Et D1-108b-1 A83 Me Me Me D1-108b-1 A84 Me Me Et D1-108b-1 A84 Me Me Me D1-108b-1 A85 Me Me Et D1-108b-1 A85 Me Me Me D1-108b-2 A91 Me Me Et D1-108b-2 A91 Me Me Me D1-108b-3 H Me Me Et D1-108b-3 H Me Me Me D1-108b-4 H Me Me Et D1-108b-4 H Me Me Me D1-108b-4 Me Me Me Et D1-108b-4 Me Me Me Me D1-108b-4 A11 Me Me Et D1-108b-4 A11 Me Me Me D1-108b-4 A34 Me Me Et D1-108b-4 A34 Me Me Me D1-108b-4 A35 Me Me Et D1-108b-4 A35 Me Me Me D1-108b-4 A37 Me Me Et D1-108b-4 A37 Me Me Me D1-108b-4 A39 Me Me Et D1-108b-4 A39 Me Me Me D1-108b-4 A40 Me Me Et D1-108b-4 A40 Me Me Me D1-108b-4 A41 Me Me Et D1-108b-4 A41 Me Me Me D1-108b-4 A73 Me Me Et D1-108b-4 A73 Me Me Me D1-108b-4 A75 Me Me Et D1-108b-4 A75 Me Me Me D1-108b-4 A83 Me Me Et D1-108b-4 A83 Me Me Me D1-108b-4 A84 Me Me Et D1-108b-4 A84 Me Me Me D1-108b-4 A85 Me Me Et D1-108b-4 A85 Me Me Me D1-108b-4 A91 Me Me Et D1-108b-4 A91 Me Me Me D1-108b-5 H Me Me Et D1-108b-5 H Me Me Me D1-108b-6 H Me Me Et D1-108b-6 H Me Me Me D1-108b-7 H Me Me Et D1-108b-7 H Me Me Me D1-108b-8 H Me Me Et D1-108b-8 H Me Me Me D1-108b-8 Me Me Me Et D1-108b-8 Me Me Me Me D1-108b-8 A11 Me Me Et D1-108b-8 A11 Me Me Me D1-108b-8 A34 Me Me Et D1-108b-8 A34 Me Me Me D1-108b-8 A35 Me Me Et D1-108b-8 A35 Me Me Me D1-108b-8 A37 Me Me Et D1-108b-8 A37 Me Me Me D1-108b-8 A39 Me Me Et D1-108b-8 A39 Me Me Me D1-108b-8 A40 Me Me Et D1-108b-8 A40 Me Me Me D1-108b-8 A41 Me Me Et D1-108b-8 A41 Me Me Me D1-108b-8 A73 Me Me Et D1-108b-8 A73 Me Me Me D1-108b-8 A75 Me Me Et D1-108b-8 A75 Me Me Me D1-108b-8 A83 Me Me Et D1-108b-8 A83 Me Me Me D1-108b-8 A84 Me Me Et D1-108b-8 A84 Me Me Me D1-108b-8 A85 Me Me Et D1-108b-8 A85 Me Me Me D1-108b-8 A91 Me Me Et D1-108b-8 A91 Me Me Me D1-108b-9 H Me Me Et D1-108b-9 H Me Me Me D1-108b-9 Me Me Me Et D1-108b-9 Me Me Me Me D1-108b-9 A11 Me Me Et D1-108b-9 A11 Me Me Me D1-108b-9 A34 Me Me Et D1-108b-9 A34 Me Me Me D1-108b-9 A35 Me Me Et D1-108b-9 A35 Me Me Me D1-108b-9 A37 Me Me Et D1-108b-9 A37 Me Me Me D1-108b-9 A39 Me Me Et D1-108b-9 A39 Me Me Me D1-108b-9 A40 Me Me Et D1-108b-9 A40 Me Me Me D1-108b-9 A41 Me Me Et D1-108b-9 A41 Me Me Me D1-108b-9 A73 Me Me Et D1-108b-9 A73 Me Me Me D1-108b-9 A75 Me Me Et D1-108b-9 A75 Me Me Me D1-108b-9 A83 Me Me Et D1-108b-9 A83 Me Me Me D1-108b-9 A84 Me Me Et D1-108b-9 A84 Me Me Me D1-108b-9 A85 Me Me Et D1-108b-9 A85 Me Me Me D1-108b-9 A91 Me Me Et D1-108b-9 A91 Me Me Me D1-108b-10 H Me Me Et D1-108b-10 H Me Me Me D1-108b-10 Me Me Me Et D1-108b-10 Me Me Me Me D1-108b-10 A11 Me Me Et D1-108b-10 A11 Me Me Me D1-108b-10 A34 Me Me Et D1-108b-10 A34 Me Me Me D1-108b-10 A35 Me Me Et D1-108b-10 A35 Me Me Me D1-108b-10 A37 Me Me Et D1-108b-10 A37 Me Me Me D1-108b-10 A39 Me Me Et D1-108b-10 A39 Me Me Me D1-108b-10 A40 Me Me Et D1-108b-10 A40 Me Me Me D1-108b-10 A41 Me Me Et D1-108b-10 A41 Me Me Me D1-108b-10 A73 Me Me Et D1-108b-10 A73 Me Me Me D1-108b-10 A75 Me Me Et D1-108b-10 A75 Me Me Me D1-108b-10 A83 Me Me Et D1-108b-10 A83 Me Me Me D1-108b-10 A84 Me Me Et D1-108b-10 A84 Me Me Me D1-108b-10 A85 Me Me Et D1-108b-10 A85 Me Me Me D1-108b-10 A91 Me Me Et D1-108b-10 A91 Me Me Me D1-108b-11 H Me Me Et D1-108b-11 H Me Me Me D1-108b-12 H Me Me Et D1-108b-12 H Me Me Me D1-108b-12 Me Me Me Et D1-108b-12 Me Me Me Me D1-108b-12 A11 Me Me Et D1-108b-12 A11 Me Me Me D1-108b-12 A34 Me Me Et D1-108b-12 A34 Me Me Me D1-108b-12 A35 Me Me Et D1-108b-12 A35 Me Me Me D1-108b-12 A37 Me Me Et D1-108b-12 A37 Me Me Me D1-108b-12 A39 Me Me Et D1-108b-12 A39 Me Me Me D1-108b-12 A40 Me Me Et D1-108b-12 A40 Me Me Me D1-108b-12 A41 Me Me Et D1-108b-12 A41 Me Me Me D1-108b-12 A73 Me Me Et D1-108b-12 A73 Me Me Me D1-108b-12 A75 Me Me Et D1-108b-12 A75 Me Me Me D1-108b-12 A83 Me Me Et D1-108b-12 A83 Me Me Me D1-108b-12 A84 Me Me Et D1-108b-12 A84 Me Me Me D1-108b-12 A85 Me Me Et D1-108b-12 A85 Me Me Me D1-108b-12 A91 Me Me Et D1-108b-12 A91 Me Me Me D1-108b-13 H Me Me Et D1-108b-13 H Me Me Me D1-108b-14 H Me Me Et D1-108b-14 H Me Me Me D1-108b-15 H Me Me Et D1-108b-15 H Me Me Me D1-108b-16 H Me Me Et D1-108b-16 H Me Me Me D1-108b-17 H Me Me Et D1-108b-17 H Me Me Me D1-108b-18 H Me Me Et D1-108b-18 H Me Me Me D1-108b-19 H Me Me Et D1-108b-19 H Me Me Me D1-2a H Me Me Et D1-2a H Me Me Me D1-2b H Me Me Et D1-2b H Me Me Me D1-7a H Me Me Et D1-7a H Me Me Me D1-7b-1 H Me Me Et D1-7b-1 H Me Me Me D1-7b-1 A39 Me Me Et D1-7b-1 A39 Me Me Me D1-7b-1 A40 Me Me Et D1-7b-1 A40 Me Me Me D1-7b-1 A41 Me Me Et D1-7b-1 A41 c-Pr Me Me D1-7b-1 H c-Pr Me Et D1-7b-1 H c-Pr Me Me D1-7b-1 A39 c-Pr Me Et D1-7b-1 A39 c-Pr Me Me D1-7b-1 A40 c-Pr Me Et D1-7b-1 A40 c-Pr Me Me D1-7b-1 A41 c-Pr Me Et D1-7b-1 A41 c-Bu Me Me D1-7b-1 H c-Bu Me Et D1-7b-1 H c-Bu Me Me D1-7b-1 A39 c-Bu Me Et D1-7b-1 A39 c-Bu Me Me D1-7b-1 A40 c-Bu Me Et D1-7b-1 A40 c-Bu Me Me D1-7b-1 A41 c-Bu Me Et D1-7b-1 A41 c-Pen Me Me D1-7b-1 H c-Pen Me Et D1-7b-1 H c-Pen Me Me D1-7b-1 A39 c-Pen Me Et D1-7b-1 A39 c-Pen Me Me D1-7b-1 A40 c-Pen Me Et D1-7b-1 A40 c-Pen Me Me D1-7b-1 A41 c-Pen Me Et D1-7b-1 A41 c-Hex Me Me D1-7b-1 H c-Hex Me Et D1-7b-1 H c-Hex Me Me D1-7b-1 A39 c-Hex Me Et D1-7b-1 A39 c-Hex Me Me D1-7b-1 A40 c-Hex Me Et D1-7b-1 A40 c-Hex Me Me D1-7b-1 A41 c-Hex Me Et D1-7b-1 A41 Me Me Me D1-7b-2 H Me Me Et D1-7b-2 H Me Me Me D1-7b-2 A39 Me Me Et D1-7b-2 A39 Me Me Me D1-7b-2 A40 Me Me Et D1-7b-2 A40 Me Me Me D1-7b-2 A41 Me Me Et D1-7b-2 A41 c-Pr Me Me D1-7b-2 H c-Pr Me Et D1-7b-2 H c-Pr Me Me D1-7b-2 A39 c-Pr Me Et D1-7b-2 A39 c-Pr Me Me D1-7b-2 A40 c-Pr Me Et D1-7b-2 A40 c-Pr Me Me D1-7b-2 A41 c-Pr Me Et D1-7b-2 A41 c-Bu Me Me D1-7b-2 H c-Bu Me Et D1-7b-2 H c-Bu Me Me D1-7b-2 A39 c-Bu Me Et D1-7b-2 A39 c-Bu Me Me D1-7b-2 A40 c-Bu Me Et D1-7b-2 A40 c-Bu Me Me D1-7b-2 A41 c-Bu Me Et D1-7b-2 A41 c-Pen Me Me D1-7b-2 H c-Pen Me Et D1-7b-2 H c-Pen Me Me D1-7b-2 A39 c-Pen Me Et D1-7b-2 A39 c-Pen Me Me D1-7b-2 A40 c-Pen Me Et D1-7b-2 A40 c-Pen Me Me D1-7b-2 A41 c-Pen Me Et D1-7b-2 A41 c-Hex Me Me D1-7b-2 H c-Hex Me Et D1-7b-2 H c-Hex Me Me D1-7b-2 A39 c-Hex Me Et D1-7b-2 A39 c-Hex Me Me D1-7b-2 A40 c-Hex Me Et D1-7b-2 A40 c-Hex Me Me D1-7b-2 A41 c-Hex Me Et D1-7b-2 A41 Me Me Me D1-7b-3 H Me Me Et D1-7b-3 H Me Me Me D1-7b-3 A39 Me Me Et D1-7b-3 A39 Me Me Me D1-7b-3 A40 Me Me Et D1-7b-3 A40 Me Me Me D1-7b-3 A41 Me Me Et D1-7b-3 A41 c-Pr Me Me D1-7b-3 H c-Pr Me Et D1-7b-3 H c-Pr Me Me D1-7b-3 A39 c-Pr Me Et D1-7b-3 A39 c-Pr Me Me D1-7b-3 A40 c-Pr Me Et D1-7b-3 A40 c-Pr Me Me D1-7b-3 A41 c-Pr Me Et D1-7b-3 A41 c-Bu Me Me D1-7b-3 H c-Bu Me Et D1-7b-3 H c-Bu Me Me D1-7b-3 A39 c-Bu Me Et D1-7b-3 A39 c-Bu Me Me D1-7b-3 A40 c-Bu Me Et D1-7b-3 A40 c-Bu Me Me D1-7b-3 A41 c-Bu Me Et D1-7b-3 A41 c-Pen Me Me D1-7b-3 H c-Pen Me Et D1-7b-3 H c-Pen Me Me D1-7b-3 A39 c-Pen Me Et D1-7b-3 A39 c-Pen Me Me D1-7b-3 A40 c-Pen Me Et D1-7b-3 A40 c-Pen Me Me D1-7b-3 A41 c-Pen Me Et D1-7b-3 A41 c-Hex Me Me D1-7b-3 H c-Hex Me Et D1-7b-3 H c-Hex Me Me D1-7b-3 A39 c-Hex Me Et D1-7b-3 A39 c-Hex Me Me D1-7b-3 A40 c-Hex Me Et D1-7b-3 A40 c-Hex Me Me D1-7b-3 A41 c-Hex Me Et D1-7b-3 A41 Me Me Me D1-7b-4 H Me Me Et D1-7b-4 H Me Me Me D1-7b-4 A39 Me Me Et D1-7b-4 A39 Me Me Me D1-7b-4 A40 Me Me Et D1-7b-4 A40 Me Me Me D1-7b-4 A41 Me Me Et D1-7b-4 A41 c-Pr Me Me D1-7b-4 H c-Pr Me Et D1-7b-4 H c-Pr Me Me D1-7b-4 A39 c-Pr Me Et D1-7b-4 A39 c-Pr Me Me D1-7b-4 A40 c-Pr Me Et D1-7b-4 A40 c-Pr Me Me D1-7b-4 A41 c-Pr Me Et D1-7b-4 A41 c-Bu Me Me D1-7b-4 H c-Bu Me Et D1-7b-4 H c-Bu Me Me D1-7b-4 A39 c-Bu Me Et D1-7b-4 A39 c-Bu Me Me D1-7b-4 A40 c-Bu Me Et D1-7b-4 A40 c-Bu Me Me D1-7b-4 A41 c-Bu Me Et D1-7b-4 A41 c-Pen Me Me D1-7b-4 H c-Pen Me Et D1-7b-4 H c-Pen Me Me D1-7b-4 A39 c-Pen Me Et D1-7b-4 A39 c-Pen Me Me D1-7b-4 A40 c-Pen Me Et D1-7b-4 A40 c-Pen Me Me D1-7b-4 A41 c-Pen Me Et D1-7b-4 A41 c-Hex Me Me D1-7b-4 H c-Hex Me Et D1-7b-4 H c-Hex Me Me D1-7b-4 A39 c-Hex Me Et D1-7b-4 A39 c-Hex Me Me D1-7b-4 A40 c-Hex Me Et D1-7b-4 A40 c-Hex Me Me D1-7b-4 A41 c-Hex Me Et D1-7b-4 A41 Me Me Me D1-10a H Me Me Et D1-10a H Me Me Me D1-11a H Me Me Et D1-11a H Me Me Me D1-11b-1 H Me Me Et D1-11b-1 H Me Me Me D1-11b-2 H Me Me Et D1-11b-2 H Me Me Me D1-11b-3 H Me Me Et D1-11b-3 H Me Me Me D1-11b-4 H Me Me Et D1-11b-4 H Me Me Me D1-22a H Me Me Et D1-22a H Me Me Me D1-22b-1 H Me Me Et D1-22b-1 H Me Me Me D1-22b-2 H Me Me Et D1-22b-2 H Me Me Me D1-22b-3 H Me Me Et D1-22b-3 H Me Me Me D1-22b-4 H Me Me Et D1-22b-4 H Me Me Me D1-32a H Me Me Et D1-32a H Me Me Me D1-32b-1 H Me Me Et D1-32b-1 H Me Me Me D1-32b-2 H Me Me Et D1-32b-2 H Me Me Me D1-32b-3 H Me Me Et D1-32b-3 H Me Me Me D1-32c-4 H Me Me Et D1-32c-4 H Me Me Me D1-32b-5 H Me Me Et D1-32b-5 H Me Me Me D1-33a H Me Me Et D1-33a H Me Me Me D1-33b-1 H Me Me Et D1-33b-1 H Me Me Me D1-33b-2 H Me Me Et D1-33b-2 H Me Me Me D1-33b-3 H Me Me Et D1-33b-3 H Me Me Me D1-33b-4 H Me Me Et D1-33b-4 H Me Me Me D1-34a H Me Me Et D1-34a H Me Me Me D1-37a H Me Me Et D1-37a H Me Me Me D1-37b-1 H Me Me Et D1-37b-1 H Me Me Me C≡CH H Me Me Et C≡CH H Me Me Me C≡CH A39 Me Me Et C≡CH A39 Me Me Me C≡CH A40 Me Me Et C≡CH A40 Me Me Me C≡CH A41 Me Me Et C≡CH A41 c-Pr Me Me C≡CH H c-Pr Me Et C≡CH H c-Pr Me Me C≡CH A39 c-Pr Me Et C≡CH A39 c-Pr Me Me C≡CH A40 c-Pr Me Et C≡CH A40 c-Pr Me Me C≡CH A41 c-Pr Me Et C≡CH A41 c-Bu Me Me C≡CH H c-Bu Me Et C≡CH H c-Bu Me Me C≡CH A39 c-Bu Me Et C≡CH A39 c-Bu Me Me C≡CH A40 c-Bu Me Et C≡CH A40 c-Bu Me Me C≡CH A41 c-Bu Me Et C≡CH A41 c-Pen Me Me C≡CH H c-Pen Me Et C≡CH H c-Pen Me Me C≡CH A39 c-Pen Me Et C≡CH A39 c-Pen Me Me C≡CH A40 c-Pen Me Et C≡CH A40 c-Pen Me Me C≡CH A41 c-Pen Me Et C≡CH A41 c-Hex Me Me C≡CH H c-Hex Me Et C≡CH H c-Hex Me Me C≡CH A39 c-Hex Me Et C≡CH A39 c-Hex Me Me C≡CH A40 c-Hex Me Et C≡CH A40 c-Hex Me Me C≡CH A41 c-Hex Me Et C≡CH A41 Me Me Me C≡CBu-c H Me Me Et C≡CBu-c H Me Me Me C≡CBu-c A39 Me Me Et C≡CBu-c A39 Me Me Me C≡CBu-c A40 Me Me Et C≡CBu-c A40 Me Me Me C≡CBu-c A41 Me Me Et C≡CBu-c A41 c-Pr Me Me C≡CBu-c H c-Pr Me Et C≡CBu-c H c-Pr Me Me C≡CBu-c A39 c-Pr Me Et C≡CBu-c A39 c-Pr Me Me C≡CBu-c A40 c-Pr Me Et C≡CBu-c A40 c-Pr Me Me C≡CBu-c A41 c-Pr Me Et C≡CBu-c A41 c-Bu Me Me C≡CBu-c H c-Bu Me Et C≡CBu-c H c-Bu Me Me C≡CBu-c A39 c-Bu Me Et C≡CBu-c A39 c-Bu Me Me C≡CBu-c A40 c-Bu Me Et C≡CBu-c A40 c-Bu Me Me C≡CBu-c A41 c-Bu Me Et C≡CBu-c A41 c-Pen Me Me C≡CBu-c H c-Pen Me Et C≡CBu-c H c-Pen Me Me C≡CBu-c A39 c-Pen Me Et C≡CBu-c A39 c-Pen Me Me C≡CBu-c A40 c-Pen Me Et C≡CBu-c A40 c-Pen Me Me C≡CBu-c A41 c-Pen Me Et C≡CBu-c A41 c-Hex Me Me C≡CBu-c H c-Hex Me Et C≡CBu-c H c-Hex Me Me C≡CBu-c A39 c-Hex Me Et C≡CBu-c A39 c-Hex Me Me C≡CBu-c A40 c-Hex Me Et C≡CBu-c A40 c-Hex Me Me C≡CBu-c A41 c-Hex Me Et C≡CBu-c A41 Me Me Me C≡CPen-c H Me Me Et C≡CPen-c H Me Me Me C≡CPen-c A39 Me Me Et C≡CPen-c A39 Me Me Me C≡CPen-c A40 Me Me Et C≡CPen-c A40 Me Me Me C≡CPen-c A41 Me Me Et C≡CPen-c A41 c-Pr Me Me C≡CPen-c H c-Pr Me Et C≡CPen-c H c-Pr Me Me C≡CPen-c A39 c-Pr Me Et C≡CPen-c A39 c-Pr Me Me C≡CPen-c A40 c-Pr Me Et C≡CPen-c A40 c-Pr Me Me C≡CPen-c A41 c-Pr Me Et C≡CPen-c A41 c-Bu Me Me C≡CPen-c H c-Bu Me Et C≡CPen-c H c-Bu Me Me C≡CPen-c A39 c-Bu Me Et C≡CPen-c A39 c-Bu Me Me C≡CPen-c A40 c-Bu Me Et C≡CPen-c A40 c-Bu Me Me C≡CPen-c A41 c-Bu Me Et C≡CPen-c A41 c-Pen Me Me C≡CPen-c H c-Pen Me Et C≡CPen-c H c-Pen Me Me C≡CPen-c A39 c-Pen Me Et C≡CPen-c A39 c-Pen Me Me C≡CPen-c A40 c-Pen Me Et C≡CPen-c A40 c-Pen Me Me C≡CPen-c A41 c-Pen Me Et C≡CPen-c A41 c-Hex Me Me C≡CPen-c H c-Hex Me Et C≡CPen-c H c-Hex Me Me C≡CPen-c A39 c-Hex Me Et C≡CPen-c A39 c-Hex Me Me C≡CPen-c A40 c-Hex Me Et C≡CPen-c A40 c-Hex Me Me C≡CPen-c A41 c-Hex Me Et C≡CPen-c A41 Me Me Me C≡CHex-c H Me Me Et C≡CHex-c H Me Me Me C≡CHex-c A39 Me Me Et C≡CHex-c A39 Me Me Me C≡CHex-c A40 Me Me Et C≡CHex-c A40 Me Me Me C≡CHex-c A41 Me Me Et C≡CHex-c A41 c-Pr Me Me C≡CHex-c H c-Pr Me Et C≡CHex-c H c-Pr Me Me C≡CHex-c A39 c-Pr Me Et C≡CHex-c A39 c-Pr Me Me C≡CHex-c A40 c-Pr Me Et C≡CHex-c A40 c-Pr Me Me C≡CHex-c A41 c-Pr Me Et C≡CHex-c A41 c-Bu Me Me C≡CHex-c H c-Bu Me Et C≡CHex-c H c-Bu Me Me C≡CHex-c A39 c-Bu Me Et C≡CHex-c A39 c-Bu Me Me C≡CHex-c A40 c-Bu Me Et C≡CHex-c A40 c-Bu Me Me C≡CHex-c A41 c-Bu Me Et C≡CHex-c A41 c-Pen Me Me C≡CHex-c H c-Pen Me Et C≡CHex-c H c-Pen Me Me C≡CHex-c A39 c-Pen Me Et C≡CHex-c A39 c-Pen Me Me C≡CHex-c A40 c-Pen Me Et C≡CHex-c A40 c-Pen Me Me C≡CHex-c A41 c-Pen Me Et C≡CHex-c A41 c-Hex Me Me C≡CHex-c H c-Hex Me Et C≡CHex-c H c-Hex Me Me C≡CHex-c A39 c-Hex Me Et C≡CHex-c A39 c-Hex Me Me C≡CHex-c A40 c-Hex Me Et C≡CHex-c A40 c-Hex Me Me C≡CHex-c A41 c-Hex Me Et C≡CHex-c A41 Me Et Et C≡CMe H Me Me n-Pr C≡CMe H Me Et Et C≡CMe A39 Me Me n-Pr C≡CMe A39 Me Et Et C≡CMe A40 Me Me n-Pr C≡CMe A40 Me Et Et C≡CMe A41 Me Me n-Pr C≡CMe A41 c-Pr Et Et C≡CMe H c-Pr Me n-Pr C≡CMe H c-Pr Et Et C≡CMe A39 c-Pr Me n-Pr C≡CMe A39 c-Pr Et Et C≡CMe A40 c-Pr Me n-Pr C≡CMe A40 c-Pr Et Et C≡CMe A41 c-Pr Me n-Pr C≡CMe A41 c-Bu Et Et C≡CMe H c-Bu Me n-Pr C≡CMe H c-Bu Et Et C≡CMe A39 c-Bu Me n-Pr C≡CMe A39 c-Bu Et Et C≡CMe A40 c-Bu Me n-Pr C≡CMe A40 c-Bu Et Et C≡CMe A41 c-Bu Me n-Pr C≡CMe A41 c-Pen Et Et C≡CMe H c-Pen Me n-Pr C≡CMe H c-Pen Et Et C≡CMe A39 c-Pen Me n-Pr C≡CMe A39 c-Pen Et Et C≡CMe A40 c-Pen Me n-Pr C≡CMe A40 c-Pen Et Et C≡CMe A41 c-Pen Me n-Pr C≡CMe A41 c-Hex Et Et C≡CMe H c-Hex Me n-Pr C≡CMe H c-Hex Et Et C≡CMe A39 c-Hex Me n-Pr C≡CMe A39 c-Hex Et Et C≡CMe A40 c-Hex Me n-Pr C≡CMe A40 c-Hex Et Et C≡CMe A41 c-Hex Me n-Pr C≡CMe A41 Me Et Et C≡CSi(Me)₃ H Me Me n-Pr C≡CSi(Me)₃ H Me Et Et C≡CSi(Me)₃ A39 Me Me n-Pr C≡CSi(Me)₃ A39 Me Et Et C≡CSi(Me)₃ A40 Me Me n-Pr C≡CSi(Me)₃ A40 Me Et Et C≡CSi(Me)₃ A41 Me Me n-Pr C≡CSi(Me)₃ A41 c-Pr Et Et C≡CSi(Me)₃ H c-Pr Me n-Pr C≡CSi(Me)₃ H c-Pr Et Et C≡CSi(Me)₃ A39 c-Pr Me n-Pr C≡CSi(Me)₃ A39 c-Pr Et Et C≡CSi(Me)₃ A40 c-Pr Me n-Pr C≡CSi(Me)₃ A40 c-Pr Et Et C≡CSi(Me)₃ A41 c-Pr Me n-Pr C≡CSi(Me)₃ A41 c-Bu Et Et C≡CSi(Me)₃ H c-Bu Me n-Pr C≡CSi(Me)₃ H c-Bu Et Et C≡CSi(Me)₃ A39 c-Bu Me n-Pr C≡CSi(Me)₃ A39 c-Bu Et Et C≡CSi(Me)₃ A40 c-Bu Me n-Pr C≡CSi(Me)₃ A40 c-Bu Et Et C≡CSi(Me)₃ A41 c-Bu Me n-Pr C≡CSi(Me)₃ A41 c-Pen Et Et C≡CSi(Me)₃ H c-Pen Me n-Pr C≡CSi(Me)₃ H c-Pen Et Et C≡CSi(Me)₃ A39 c-Pen Me n-Pr C≡CSi(Me)₃ A39 c-Pen Et Et C≡CSi(Me)₃ A40 c-Pen Me n-Pr C≡CSi(Me)₃ A40 c-Pen Et Et C≡CSi(Me)₃ A41 c-Pen Me n-Pr C≡CSi(Me)₃ A41 c-Hex Et Et C≡CSi(Me)₃ H c-Hex Me n-Pr C≡CSi(Me)₃ H c-Hex Et Et C≡CSi(Me)₃ A39 c-Hex Me n-Pr C≡CSi(Me)₃ A39 c-Hex Et Et C≡CSi(Me)₃ A40 c-Hex Me n-Pr C≡CSi(Me)₃ A40 c-Hex Et Et C≡CSi(Me)₃ A41 c-Hex Me n-Pr C≡CSi(Me)₃ A41 Me Et Et C≡CPr-c H Me Me n-Pr C≡CPr-c H Me Et Et C≡CPr-c A39 Me Me n-Pr C≡CPr-c A39 Me Et Et C≡CPr-c A40 Me Me n-Pr C≡CPr-c A40 Me Et Et C≡CPr-c A41 Me Me n-Pr C≡CPr-c A41 c-Pr Et Et C≡CPr-c H c-Pr Me n-Pr C≡CPr-c H c-Pr Et Et C≡CPr-c A39 c-Pr Me n-Pr C≡CPr-c A39 c-Pr Et Et C≡CPr-c A40 c-Pr Me n-Pr C≡CPr-c A40 c-Pr Et Et C≡CPr-c A41 c-Pr Me n-Pr C≡CPr-c A41 c-Bu Et Et C≡CPr-c H c-Bu Me n-Pr C≡CPr-c H c-Bu Et Et C≡CPr-c A39 c-Bu Me n-Pr C≡CPr-c A39 c-Bu Et Et C≡CPr-c A40 c-Bu Me n-Pr C≡CPr-c A40 c-Bu Et Et C≡CPr-c A41 c-Bu Me n-Pr C≡CPr-c A41 c-Pen Et Et C≡CPr-c H c-Pen Me n-Pr C≡CPr-c H c-Pen Et Et C≡CPr-c A39 c-Pen Me n-Pr C≡CPr-c A39 c-Pen Et Et C≡CPr-c A40 c-Pen Me n-Pr C≡CPr-c A40 c-Pen Et Et C≡CPr-c A41 c-Pen Me n-Pr C≡CPr-c A41 c-Hex Et Et C≡CPr-c H c-Hex Me n-Pr C≡CPr-c H c-Hex Et Et C≡CPr-c A39 c-Hex Me n-Pr C≡CPr-c A39 c-Hex Et Et C≡CPr-c A40 c-Hex Me n-Pr C≡CPr-c A40 c-Hex Et Et C≡CPr-c A41 c-Hex Me n-Pr C≡CPr-c A41 Me Et Et C≡CC(Me)₂OH H Me Me n-Pr C≡CC(Me)₂OH H Me Et Et C≡CC(Me)₂OH A39 Me Me n-Pr C≡CC(Me)₂OH A39 Me Et Et C≡CC(Me)₂OH A40 Me Me n-Pr C≡CC(Me)₂OH A40 Me Et Et C≡CC(Me)₂OH A41 Me Me n-Pr C≡CC(Me)₂OH A41 Me Et Et C≡CCH₂OH H Me Me n-Pr C≡CCH₂OH H Me Et Et C≡CCH₂OH A39 Me Me n-Pr C≡CCH₂OH A39 Me Et Et C≡CCH₂OH A40 Me Me n-Pr C≡CCH₂OH A40 Me Et Et C≡CCH₂OH A41 Me Me n-Pr C≡CCH₂OH A41 Me Et Et Ph H Me Me n-Pr Ph H Me Et Et Ph Me Me Me n-Pr Ph Me Me Et Et Ph A11 Me Me n-Pr Ph A11 Me Et Et Ph A34 Me Me n-Pr Ph A34 Me Et Et Ph A35 Me Me n-Pr Ph A35 Me Et Et Ph A37 Me Me n-Pr Ph A37 Me Et Et Ph A39 Me Me n-Pr Ph A39 Me Et Et Ph A40 Me Me n-Pr Ph A40 Me Et Et Ph A41 Me Me n-Pr Ph A41 Me Et Et Ph A73 Me Me n-Pr Ph A73 Me Et Et Ph A75 Me Me n-Pr Ph A75 Me Et Et Ph A83 Me Me n-Pr Ph A83 Me Et Et Ph A84 Me Me n-Pr Ph A84 Me Et Et Ph A85 Me Me n-Pr Ph A85 Me Et Et Ph A91 Me Me n-Pr Ph A91 Me Et Et D1-108b-1 H Me Me n-Pr D1-108b-1 H Me Et Et D1-108b-1 Me Me Me n-Pr D1-108b-1 Me Me Et Et D1-108b-1 A11 Me Me n-Pr D1-108b-1 A11 Me Et Et D1-108b-1 A34 Me Me n-Pr D1-108b-1 A34 Me Et Et D1-108b-1 A35 Me Me n-Pr D1-108b-1 A35 Me Et Et D1-108b-1 A37 Me Me n-Pr D1-108b-1 A37 Me Et Et D1-108b-1 A39 Me Me n-Pr D1-108b-1 A39 Me Et Et D1-108b-1 A40 Me Me n-Pr D1-108b-1 A40 Me Et Et D1-108b-1 A41 Me Me n-Pr D1-108b-1 A41 Me Et Et D1-108b-1 A73 Me Me n-Pr D1-108b-1 A73 Me Et Et D1-108b-1 A75 Me Me n-Pr D1-108b-1 A75 Me Et Et D1-108b-1 A83 Me Me n-Pr D1-108b-1 A83 Me Et Et D1-108b-1 A84 Me Me n-Pr D1-108b-1 A84 Me Et Et D1-108b-1 A85 Me Me n-Pr D1-108b-1 A85 Me Et Et D1-108b-2 A91 Me Me n-Pr D1-108b-2 A91 Me Et Et D1-108b-3 H Me Me n-Pr D1-108b-3 H Me Et Et D1-108b-4 H Me Me n-Pr D1-108b-4 H Me Et Et D1-108b-4 Me Me Me n-Pr D1-108b-4 Me Me Et Et D1-108b-4 A11 Me Me n-Pr D1-108b-4 A11 Me Et Et D1-108b-4 A34 Me Me n-Pr D1-108b-4 A34 Me Et Et D1-108b-4 A35 Me Me n-Pr D1-108b-4 A35 Me Et Et D1-108b-4 A37 Me Me n-Pr D1-108b-4 A37 Me Et Et D1-108b-4 A39 Me Me n-Pr D1-108b-4 A39 Me Et Et D1-108b-4 A40 Me Me n-Pr D1-108b-4 A40 Me Et Et D1-108b-4 A41 Me Me n-Pr D1-108b-4 A41 Me Et Et D1-108b-4 A73 Me Me n-Pr D1-108b-4 A73 Me Et Et D1-108b-4 A75 Me Me n-Pr D1-108b-4 A75 Me Et Et D1-108b-4 A83 Me Me n-Pr D1-108b-4 A83 Me Et Et D1-108b-4 A84 Me Me n-Pr D1-108b-4 A84 Me Et Et D1-108b-4 A85 Me Me n-Pr D1-108b-4 A85 Me Et Et D1-108b-4 A91 Me Me n-Pr D1-108b-4 A91 Me Et Et D1-108b-5 H Me Me n-Pr D1-108b-5 H Me Et Et D1-108b-6 H Me Me n-Pr D1-108b-6 H Me Et Et D1-108b-7 H Me Me n-Pr D1-108b-7 H Me Et Et D1-108b-8 H Me Me n-Pr D1-108b-8 H Me Et Et D1-108b-8 Me Me Me n-Pr D1-108b-8 Me Me Et Et D1-108b-8 A11 Me Me n-Pr D1-108b-8 A11 Me Et Et D1-108b-8 A34 Me Me n-Pr D1-108b-8 A34 Me Et Et D1-108b-8 A35 Me Me n-Pr D1-108b-8 A35 Me Et Et D1-108b-8 A37 Me Me n-Pr D1-108b-8 A37 Me Et Et D1-108b-8 A39 Me Me n-Pr D1-108b-8 A39 Me Et Et D1-108b-8 A40 Me Me n-Pr D1-108b-8 A40 Me Et Et D1-108b-8 A41 Me Me n-Pr D1-108b-8 A41 Me Et Et D1-108b-8 A73 Me Me n-Pr D1-108b-8 A73 Me Et Et D1-108b-8 A75 Me Me n-Pr D1-108b-8 A75 Me Et Et D1-108b-8 A83 Me Me n-Pr D1-108b-8 A83 Me Et Et D1-108b-8 A84 Me Me n-Pr D1-108b-8 A84 Me Et Et D1-108b-8 A85 Me Me n-Pr D1-108b-8 A85 Me Et Et D1-108b-8 A91 Me Me n-Pr D1-108b-8 A91 Me Et Et D1-108b-9 H Me Me n-Pr D1-108b-9 H Me Et Et D1-108b-9 Me Me Me n-Pr D1-108b-9 Me Me Et Et D1-108b-9 A11 Me Me n-Pr D1-108b-9 A11 Me Et Et D1-108b-9 A34 Me Me n-Pr D1-108b-9 A34 Me Et Et D1-108b-9 A35 Me Me n-Pr D1-108b-9 A35 Me Et Et D1-108b-9 A37 Me Me n-Pr D1-108b-9 A37 Me Et Et D1-108b-9 A39 Me Me n-Pr D1-108b-9 A39 Me Et Et D1-108b-9 A40 Me Me n-Pr D1-108b-9 A40 Me Et Et D1-108b-9 A41 Me Me n-Pr D1-108b-9 A41 Me Et Et D1-108b-9 A73 Me Me n-Pr D1-108b-9 A73 Me Et Et D1-108b-9 A75 Me Me n-Pr D1-108b-9 A75 Me Et Et D1-108b-9 A83 Me Me n-Pr D1-108b-9 A83 Me Et Et D1-108b-9 A84 Me Me n-Pr D1-108b-9 A84 Me Et Et D1-108b-9 A85 Me Me n-Pr D1-108b-9 A85 Me Et Et D1-108b-9 A91 Me Me n-Pr D1-108b-9 A91 Me Et Et D1-108b-10 H Me Me n-Pr D1-108b-10 H Me Et Et D1-108b-10 Me Me Me n-Pr D1-108b-10 Me Me Et Et D1-108b-10 A11 Me Me n-Pr D1-108b-10 A11 Me Et Et D1-108b-10 A34 Me Me n-Pr D1-108b-10 A34 Me Et Et D1-108b-10 A35 Me Me n-Pr D1-108b-10 A35 Me Et Et D1-108b-10 A37 Me Me n-Pr D1-108b-10 A37 Me Et Et D1-108b-10 A39 Me Me n-Pr D1-108b-10 A39 Me Et Et D1-108b-10 A40 Me Me n-Pr D1-108b-10 A40 Me Et Et D1-108b-10 A41 Me Me n-Pr D1-108b-10 A41 Me Et Et D1-108b-10 A73 Me Me n-Pr D1-108b-10 A73 Me Et Et D1-108b-10 A75 Me Me n-Pr D1-108b-10 A75 Me Et Et D1-108b-10 A83 Me Me n-Pr D1-108b-10 A83 Me Et Et D1-108b-10 A84 Me Me n-Pr D1-108b-10 A84 Me Et Et D1-108b-10 A85 Me Me n-Pr D1-108b-10 A85 Me Et Et D1-108b-10 A91 Me Me n-Pr D1-108b-10 A91 Me Et Et D1-108b-11 H Me Me n-Pr D1-108b-11 H Me Et Et D1-108b-12 H Me Me n-Pr D1-108b-12 H Me Et Et D1-108b-12 Me Me Me n-Pr D1-108b-12 Me Me Et Et D1-108b-12 A11 Me Me n-Pr D1-108b-12 A11 Me Et Et D1-108b-12 A34 Me Me n-Pr D1-108b-12 A34 Me Et Et D1-108b-12 A35 Me Me n-Pr D1-108b-12 A35 Me Et Et D1-108b-12 A37 Me Me n-Pr D1-108b-12 A37 Me Et Et D1-108b-12 A39 Me Me n-Pr D1-108b-12 A39 Me Et Et D1-108b-12 A40 Me Me n-Pr D1-108b-12 A40 Me Et Et D1-108b-12 A41 Me Me n-Pr D1-108b-12 A41 Me Et Et D1-108b-12 A73 Me Me n-Pr D1-108b-12 A73 Me Et Et D1-108b-12 A75 Me Me n-Pr D1-108b-12 A75 Me Et Et D1-108b-12 A83 Me Me n-Pr D1-108b-12 A83 Me Et Et D1-108b-12 A84 Me Me n-Pr D1-108b-12 A84 Me Et Et D1-108b-12 A85 Me Me n-Pr D1-108b-12 A85 Me Et Et D1-108b-12 A91 Me Me n-Pr D1-108b-12 A91 Me Et Et D1-108b-13 H Me Me n-Pr D1-108b-13 H Me Et Et D1-108b-14 H Me Me n-Pr D1-108b-14 H Me Et Et D1-108b-15 H Me Me n-Pr D1-108b-15 H Me Et Et D1-108b-16 H Me Me n-Pr D1-108b-16 H Me Et Et D1-108b-17 H Me Me n-Pr D1-108b-17 H Me Et Et D1-108b-18 H Me Me n-Pr D1-108b-18 H Me Et Et D1-108b-19 H Me Me n-Pr D1-108b-19 H Me Et Et D1-2a H Me Me n-Pr D1-2a H Me Et Et D1-2b H Me Me n-Pr D1-2b H Me Et Et D1-7a H Me Me n-Pr D1-7a H Me Et Et D1-7b-1 H Me Me n-Pr D1-7b-1 H Me Et Et D1-7b-1 A39 Me Me n-Pr D1-7b-1 A39 Me Et Et D1-7b-1 A40 Me Me n-Pr D1-7b-1 A40 Me Et Et D1-7b-1 A41 Me Me n-Pr D1-7b-1 A41 c-Pr Et Et D1-7b-1 H c-Pr Me n-Pr D1-7b-1 H c-Pr Et Et D1-7b-1 A39 c-Pr Me n-Pr D1-7b-1 A39 c-Pr Et Et D1-7b-1 A40 c-Pr Me n-Pr D1-7b-1 A40 c-Pr Et Et D1-7b-1 A41 c-Pr Me n-Pr D1-7b-1 A41 c-Bu Et Et D1-7b-1 H c-Bu Me n-Pr D1-7b-1 H c-Bu Et Et D1-7b-1 A39 c-Bu Me n-Pr D1-7b-1 A39 c-Bu Et Et D1-7b-1 A40 c-Bu Me n-Pr D1-7b-1 A40 c-Bu Et Et D1-7b-1 A41 c-Bu Me n-Pr D1-7b-1 A41 c-Pen Et Et D1-7b-1 H c-Pen Me n-Pr D1-7b-1 H c-Pen Et Et D1-7b-1 A39 c-Pen Me n-Pr D1-7b-1 A39 c-Pen Et Et D1-7b-1 A40 c-Pen Me n-Pr D1-7b-1 A40 c-Pen Et Et D1-7b-1 A41 c-Pen Me n-Pr D1-7b-1 A41 c-Hex Et Et D1-7b-1 H c-Hex Me n-Pr D1-7b-1 H c-Hex Et Et D1-7b-1 A39 c-Hex Me n-Pr D1-7b-1 A39 c-Hex Et Et D1-7b-1 A40 c-Hex Me n-Pr D1-7b-1 A40 c-Hex Et Et D1-7b-1 A41 c-Hex Me n-Pr D1-7b-1 A41 Me Et Et D1-7b-2 H Me Me n-Pr D1-7b-2 H Me Et Et D1-7b-2 A39 Me Me n-Pr D1-7b-2 A39 Me Et Et D1-7b-2 A40 Me Me n-Pr D1-7b-2 A40 Me Et Et D1-7b-2 A41 Me Me n-Pr D1-7b-2 A41 c-Pr Et Et D1-7b-2 H c-Pr Me n-Pr D1-7b-2 H c-Pr Et Et D1-7b-2 A39 c-Pr Me n-Pr D1-7b-2 A39 c-Pr Et Et D1-7b-2 A40 c-Pr Me n-Pr D1-7b-2 A40 c-Pr Et Et D1-7b-2 A41 c-Pr Me n-Pr D1-7b-2 A41 c-Bu Et Et D1-7b-2 H c-Bu Me n-Pr D1-7b-2 H c-Bu Et Et D1-7b-2 A39 c-Bu Me n-Pr D1-7b-2 A39 c-Bu Et Et D1-7b-2 A40 c-Bu Me n-Pr D1-7b-2 A40 c-Bu Et Et D1-7b-2 A41 c-Bu Me n-Pr D1-7b-2 A41 c-Pen Et Et D1-7b-2 H c-Pen Me n-Pr D1-7b-2 H c-Pen Et Et D1-7b-2 A39 c-Pen Me n-Pr D1-7b-2 A39 c-Pen Et Et D1-7b-2 A40 c-Pen Me n-Pr D1-7b-2 A40 c-Pen Et Et D1-7b-2 A41 c-Pen Me n-Pr D1-7b-2 A41 c-Hex Et Et D1-7b-2 H c-Hex Me n-Pr D1-7b-2 H c-Hex Et Et D1-7b-2 A39 c-Hex Me n-Pr D1-7b-2 A39 c-Hex Et Et D1-7b-2 A40 c-Hex Me n-Pr D1-7b-2 A40 c-Hex Et Et D1-7b-2 A41 c-Hex Me n-Pr D1-7b-2 A41 Me Et Et D1-7b-3 H Me Me n-Pr D1-7b-3 H Me Et Et D1-7b-3 A39 Me Me n-Pr D1-7b-3 A39 Me Et Et D1-7b-3 A40 Me Me n-Pr D1-7b-3 A40 Me Et Et D1-7b-3 A41 Me Me n-Pr D1-7b-3 A41 c-Pr Et Et D1-7b-3 H c-Pr Me n-Pr D1-7b-3 H c-Pr Et Et D1-7b-3 A39 c-Pr Me n-Pr D1-7b-3 A39 c-Pr Et Et D1-7b-3 A40 c-Pr Me n-Pr D1-7b-3 A40 c-Pr Et Et D1-7b-3 A41 c-Pr Me n-Pr D1-7b-3 A41 c-Bu Et Et D1-7b-3 H c-Bu Me n-Pr D1-7b-3 H c-Bu Et Et D1-7b-3 A39 c-Bu Me n-Pr D1-7b-3 A39 c-Bu Et Et D1-7b-3 A40 c-Bu Me n-Pr D1-7b-3 A40 c-Bu Et Et D1-7b-3 A41 c-Bu Me n-Pr D1-7b-3 A41 c-Pen Et Et D1-7b-3 H c-Pen Me n-Pr D1-7b-3 H c-Pen Et Et D1-7b-3 A39 c-Pen Me n-Pr D1-7b-3 A39 c-Pen Et Et D1-7b-3 A40 c-Pen Me n-Pr D1-7b-3 A40 c-Pen Et Et D1-7b-3 A41 c-Pen Me n-Pr D1-7b-3 A41 c-Hex Et Et D1-7b-3 H c-Hex Me n-Pr D1-7b-3 H c-Hex Et Et D1-7b-3 A39 c-Hex Me n-Pr D1-7b-3 A39 c-Hex Et Et D1-7b-3 A40 c-Hex Me n-Pr D1-7b-3 A40 c-Hex Et Et D1-7b-3 A41 c-Hex Me n-Pr D1-7b-3 A41 Me Et Et D1-7b-4 H Me Me n-Pr D1-7b-4 H Me Et Et D1-7b-4 A39 Me Me n-Pr D1-7b-4 A39 Me Et Et D1-7b-4 A40 Me Me n-Pr D1-7b-4 A40 Me Et Et D1-7b-4 A41 Me Me n-Pr D1-7b-4 A41 c-Pr Et Et D1-7b-4 H c-Pr Me n-Pr D1-7b-4 H c-Pr Et Et D1-7b-4 A39 c-Pr Me n-Pr D1-7b-4 A39 c-Pr Et Et D1-7b-4 A40 c-Pr Me n-Pr D1-7b-4 A40 c-Pr Et Et D1-7b-4 A41 c-Pr Me n-Pr D1-7b-4 A41 c-Bu Et Et D1-7b-4 H c-Bu Me n-Pr D1-7b-4 H c-Bu Et Et D1-7b-4 A39 c-Bu Me n-Pr D1-7b-4 A39 c-Bu Et Et D1-7b-4 A40 c-Bu Me n-Pr D1-7b-4 A40 c-Bu Et Et D1-7b-4 A41 c-Bu Me n-Pr D1-7b-4 A41 c-Pen Et Et D1-7b-4 H c-Pen Me n-Pr D1-7b-4 H c-Pen Et Et D1-7b-4 A39 c-Pen Me n-Pr D1-7b-4 A39 c-Pen Et Et D1-7b-4 A40 c-Pen Me n-Pr D1-7b-4 A40 c-Pen Et Et D1-7b-4 A41 c-Pen Me n-Pr D1-7b-4 A41 c-Hex Et Et D1-7b-4 H c-Hex Me n-Pr D1-7b-4 H c-Hex Et Et D1-7b-4 A39 c-Hex Me n-Pr D1-7b-4 A39 c-Hex Et Et D1-7b-4 A40 c-Hex Me n-Pr D1-7b-4 A40 c-Hex Et Et D1-7b-4 A41 c-Hex Me n-Pr D1-7b-4 A41 Me Et Et D1-10a H Me Me n-Pr D1-10a H Me Et Et D1-11a H Me Me n-Pr D1-11a H Me Et Et D1-11b-1 H Me Me n-Pr D1-11b-1 H Me Et Et D1-11b-2 H Me Me n-Pr D1-11b-2 H Me Et Et D1-11b-3 H Me Me n-Pr D1-11b-3 H Me Et Et D1-11b-4 H Me Me n-Pr D1-11b-4 H Me Et Et D1-22a H Me Me n-Pr D1-22a H Me Et Et D1-22b-1 H Me Me n-Pr D1-22b-1 H Me Et Et D1-22b-2 H Me Me n-Pr D1-22b-2 H Me Et Et D1-22b-3 H Me Me n-Pr D1-22b-3 H Me Et Et D1-22b-4 H Me Me n-Pr D1-22b-4 H Me Et Et D1-32a H Me Me n-Pr D1-32a H Me Et Et D1-32b-1 H Me Me n-Pr D1-32b-1 H Me Et Et D1-32b-2 H Me Me n-Pr D1-32b-2 H Me Et Et D1-32b-3 H Me Me n-Pr D1-32b-3 H Me Et Et D1-32c-4 H Me Me n-Pr D1-32c-4 H Me Et Et D1-32b-5 H Me Me n-Pr D1-32b-5 H Me Et Et D1-33a H Me Me n-Pr D1-33a H Me Et Et D1-33b-1 H Me Me n-Pr D1-33b-1 H Me Et Et D1-33b-2 H Me Me n-Pr D1-33b-2 H Me Et Et D1-33b-3 H Me Me n-Pr D1-33b-3 H Me Et Et D1-33b-4 H Me Me n-Pr D1-33b-4 H Me Et Et D1-34a H Me Me n-Pr D1-34a H Me Et Et D1-37a H Me Me n-Pr D1-37a H Me Et Et D1-37b-1 H Me Me n-Pr D1-37b-1 H Me Et Et C≡CH H Me Me n-Pr C≡CH H Me Et Et C≡CH A39 Me Me n-Pr C≡CH A39 Me Et Et C≡CH A40 Me Me n-Pr C≡CH A40 Me Et Et C≡CH A41 Me Me n-Pr C≡CH A41 c-Pr Et Et C≡CH H c-Pr Me n-Pr C≡CH H c-Pr Et Et C≡CH A39 c-Pr Me n-Pr C≡CH A39 c-Pr Et Et C≡CH A40 c-Pr Me n-Pr C≡CH A40 c-Pr Et Et C≡CH A41 c-Pr Me n-Pr C≡CH A41 c-Bu Et Et C≡CH H c-Bu Me n-Pr C≡CH H c-Bu Et Et C≡CH A39 c-Bu Me n-Pr C≡CH A39 c-Bu Et Et C≡CH A40 c-Bu Me n-Pr C≡CH A40 c-Bu Et Et C≡CH A41 c-Bu Me n-Pr C≡CH A41 c-Pen Et Et C≡CH H c-Pen Me n-Pr C≡CH H c-Pen Et Et C≡CH A39 c-Pen Me n-Pr C≡CH A39 c-Pen Et Et C≡CH A40 c-Pen Me n-Pr C≡CH A40 c-Pen Et Et C≡CH A41 c-Pen Me n-Pr C≡CH A41 c-Hex Et Et C≡CH H c-Hex Me n-Pr C≡CH H c-Hex Et Et C≡CH A39 c-Hex Me n-Pr C≡CH A39 c-Hex Et Et C≡CH A40 c-Hex Me n-Pr C≡CH A40 c-Hex Et Et C≡CH A41 c-Hex Me n-Pr C≡CH A41 Me Et Et C≡CBu-c H Me Me n-Pr C≡CBu-c H Me Et Et C≡CBu-c A39 Me Me n-Pr C≡CBu-c A39 Me Et Et C≡CBu-c A40 Me Me n-Pr C≡CBu-c A40 Me Et Et C≡CBu-c A41 Me Me n-Pr C≡CBu-c A41 c-Pr Et Et C≡CBu-c H c-Pr Me n-Pr C≡CBu-c H c-Pr Et Et C≡CBu-c A39 c-Pr Me n-Pr C≡CBu-c A39 c-Pr Et Et C≡CBu-c A40 c-Pr Me n-Pr C≡CBu-c A40 c-Pr Et Et C≡CBu-c A41 c-Pr Me n-Pr C≡CBu-c A41 c-Bu Et Et C≡CBu-c H c-Bu Me n-Pr C≡CBu-c H c-Bu Et Et C≡CBu-c A39 c-Bu Me n-Pr C≡CBu-c A39 c-Bu Et Et C≡CBu-c A40 c-Bu Me n-Pr C≡CBu-c A40 c-Bu Et Et C≡CBu-c A41 c-Bu Me n-Pr C≡CBu-c A41 c-Pen Et Et C≡CBu-c H c-Pen Me n-Pr C≡CBu-c H c-Pen Et Et C≡CBu-c A39 c-Pen Me n-Pr C≡CBu-c A39 c-Pen Et Et C≡CBu-c A40 c-Pen Me n-Pr C≡CBu-c A40 c-Pen Et Et C≡CBu-c A41 c-Pen Me n-Pr C≡CBu-c A41 c-Hex Et Et C≡CBu-c H c-Hex Me n-Pr C≡CBu-c H c-Hex Et Et C≡CBu-c A39 c-Hex Me n-Pr C≡CBu-c A39 c-Hex Et Et C≡CBu-c A40 c-Hex Me n-Pr C≡CBu-c A40 c-Hex Et Et C≡CBu-c A41 c-Hex Me n-Pr C≡CBu-c A41 Me Et Et C≡CPen-c H Me Me n-Pr C≡CPen-c H Me Et Et C≡CPen-c A39 Me Me n-Pr C≡CPen-c A39 Me Et Et C≡CPen-c A40 Me Me n-Pr C≡CPen-c A40 Me Et Et C≡CPen-c A41 Me Me n-Pr C≡CPen-c A41 c-Pr Et Et C≡CPen-c H c-Pr Me n-Pr C≡CPen-c H c-Pr Et Et C≡CPen-c A39 c-Pr Me n-Pr C≡CPen-c A39 c-Pr Et Et C≡CPen-c A40 c-Pr Me n-Pr C≡CPen-c A40 c-Pr Et Et C≡CPen-c A41 c-Pr Me n-Pr C≡CPen-c A41 c-Bu Et Et C≡CPen-c H c-Bu Me n-Pr C≡CPen-c H c-Bu Et Et C≡CPen-c A39 c-Bu Me n-Pr C≡CPen-c A39 c-Bu Et Et C≡CPen-c A40 c-Bu Me n-Pr C≡CPen-c A40 c-Bu Et Et C≡CPen-c A41 c-Bu Me n-Pr C≡CPen-c A41 c-Pen Et Et C≡CPen-c H c-Pen Me n-Pr C≡CPen-c H c-Pen Et Et C≡CPen-c A39 c-Pen Me n-Pr C≡CPen-c A39 c-Pen Et Et C≡CPen-c A40 c-Pen Me n-Pr C≡CPen-c A40 c-Pen Et Et C≡CPen-c A41 c-Pen Me n-Pr C≡CPen-c A41 c-Hex Et Et C≡CPen-c H c-Hex Me n-Pr C≡CPen-c H c-Hex Et Et C≡CPen-c A39 c-Hex Me n-Pr C≡CPen-c A39 c-Hex Et Et C≡CPen-c A40 c-Hex Me n-Pr C≡CPen-c A40 c-Hex Et Et C≡CPen-c A41 c-Hex Me n-Pr C≡CPen-c A41 Me Et Et C≡CHex-c H Me Me n-Pr C≡CHex-c H Me Et Et C≡CHex-c A39 Me Me n-Pr C≡CHex-c A39 Me Et Et C≡CHex-c A40 Me Me n-Pr C≡CHex-c A40 Me Et Et C≡CHex-c A41 Me Me n-Pr C≡CHex-c A41 c-Pr Et Et C≡CHex-c H c-Pr Me n-Pr C≡CHex-c H c-Pr Et Et C≡CHex-c A39 c-Pr Me n-Pr C≡CHex-c A39 c-Pr Et Et C≡CHex-c A40 c-Pr Me n-Pr C≡CHex-c A40 c-Pr Et Et C≡CHex-c A41 c-Pr Me n-Pr C≡CHex-c A41 c-Bu Et Et C≡CHex-c H c-Bu Me n-Pr C≡CHex-c H c-Bu Et Et C≡CHex-c A39 c-Bu Me n-Pr C≡CHex-c A39 c-Bu Et Et C≡CHex-c A40 c-Bu Me n-Pr C≡CHex-c A40 c-Bu Et Et C≡CHex-c A41 c-Bu Me n-Pr C≡CHex-c A41 c-Pen Et Et C≡CHex-c H c-Pen Me n-Pr C≡CHex-c H c-Pen Et Et C≡CHex-c A39 c-Pen Me n-Pr C≡CHex-c A39 c-Pen Et Et C≡CHex-c A40 c-Pen Me n-Pr C≡CHex-c A40 c-Pen Et Et C≡CHex-c A41 c-Pen Me n-Pr C≡CHex-c A41 c-Hex Et Et C≡CHex-c H c-Hex Me n-Pr C≡CHex-c H c-Hex Et Et C≡CHex-c A39 c-Hex Me n-Pr C≡CHex-c A39 c-Hex Et Et C≡CHex-c A40 c-Hex Me n-Pr C≡CHex-c A40 c-Hex Et Et C≡CHex-c A41 c-Hex Me n-Pr C≡CHex-c A41 Me Me Me Ph A74 Me Me Et Ph A74 Me Me Me D1-108b-1 A74 Me Me Et D1-108b-1 A74 Me Me Me D1-108b-2 H Me Me Et D1-108b-2 H Me Me Me D1-108b-4 A74 Me Me Et D1-108b-4 A74 Me Me Me D1-108b-8 A74 Me Me Et D1-108b-8 A74 Me Me Me D1-108b-9 A74 Me Me Et D1-108b-9 A74 Me Me Me D1-108b-10 A74 Me Me Et D1-108b-10 A74 Me Me Me D1-108b-12 A74 Me Me Et D1-108b-12 A74 Me Et Et Ph A74 Me Me n-Pr Ph A74 Me Et Et D1-108b-1 A74 Me Me n-Pr D1-108b-1 A74 Me Et Et D1-108b-2 H Me Me n-Pr D1-108b-2 H Me Et Et D1-108b-4 A74 Me Me n-Pr D1-108b-4 A74 Me Et Et D1-108b-8 A74 Me Me n-Pr D1-108b-8 A74 Me Et Et D1-108b-9 A74 Me Me n-Pr D1-108b-9 A74 Me Et Et D1-108b-10 A74 Me Me n-Pr D1-108b-10 A74 Me Et Et D1-108b-12 A74 Me Me n-Pr D1-108b-12 A74

TABLE 3

R⁶ Z^(a) Z^(c) Z^(e) A R⁶ Z^(a) Z^(c) Z^(e) A Me OMe Me Me H Me OMe Et Me H Me OMe Me Me A13 Me OMe Et Me A13 Me OMe Me Me A14 Me OMe Et Me A14 Me OMe Me Me A16 Me OMe Et Me A16 Me OMe Me Me A35 Me OMe Et Me A35 Me OMe Me Me A38 Me OMe Et Me A38 Me OMe Me Me A39 Me OMe Et Me A39 Me OMe Me Me A40 Me OMe Et Me A40 Me OMe Me Me A41 Me OMe Et Me A41 Me OMe Me Me A73 Me OMe Et Me A73 Me OMe Me Me A74 Me OMe Et Me A74 Me OMe Me Me A75 Me OMe Et Me A75 Me OMe Me Me A81 Me OMe Et Me A81 Me OMe Me Me A82 Me OMe Et Me A82 Me OMe Me Me A83 Me OMe Et Me A83 Me OMe Me Me A84 Me OMe Et Me A84 Me OMe Me Me A85 Me OMe Et Me A85 Me OMe Me Me A86 Me OMe Et Me A86 Me OMe Me Me A87 Me OMe Et Me A87 Me OMe Me Me A91 Me OMe Et Me A91 Me OMe Me Me A92 Me OMe Et Me A92 Me OMe Me Me A93 Me OMe Et Me A93 Me OMe Me Me A94 Me OMe Et Me A94 Me OMe Me Me A95 Me OMe Et Me A95 Me OMe Me Me A97 Me OMe Et Me A97 Et OMe Me Me H Et OMe Et Me H Et OMe Me Me A13 Et OMe Et Me A13 Et OMe Me Me A14 Et OMe Et Me A14 Et OMe Me Me A16 Et OMe Et Me A16 Et OMe Me Me A35 Et OMe Et Me A35 Et OMe Me Me A38 Et OMe Et Me A38 Et OMe Me Me A39 Et OMe Et Me A39 Et OMe Me Me A40 Et OMe Et Me A40 Et OMe Me Me A41 Et OMe Et Me A41 Et OMe Me Me A73 Et OMe Et Me A73 Et OMe Me Me A74 Et OMe Et Me A74 Et OMe Me Me A75 Et OMe Et Me A75 Et OMe Me Me A81 Et OMe Et Me A81 Et OMe Me Me A82 Et OMe Et Me A82 Me OMe n-Pr Me H Me OEt Me Me H Me OMe n-Pr Me A13 Me OEt Me Me A13 Me OMe n-Pr Me A14 Me OEt Me Me A14 Me OMe n-Pr Me A16 Me OEt Me Me A16 Me OMe n-Pr Me A35 Me OEt Me Me A35 Me OMe n-Pr Me A38 Me OEt Me Me A38 Me OMe n-Pr Me A39 Me OEt Me Me A39 Me OMe n-Pr Me A40 Me OEt Me Me A40 Me OMe n-Pr Me A41 Me OEt Me Me A41 Me OMe n-Pr Me A73 Me OEt Me Me A73 Me OMe n-Pr Me A74 Me OEt Me Me A74 Me OMe n-Pr Me A75 Me OEt Me Me A75 Me OMe n-Pr Me A81 Me OEt Me Me A81 Me OMe n-Pr Me A82 Me OEt Me Me A82 Me OMe n-Pr Me A83 Me OEt Me Me A83 Me OMe n-Pr Me A84 Me OEt Me Me A84 Me OMe n-Pr Me A85 Me OEt Me Me A85 Me OMe n-Pr Me A86 Me OEt Me Me A86 Me OMe n-Pr Me A87 Me OEt Me Me A87 Me OMe n-Pr Me A91 Me OEt Me Me A91 Me OMe n-Pr Me A92 Me OEt Me Me A92 Me OMe n-Pr Me A93 Me OEt Me Me A93 Me OMe n-Pr Me A94 Me OEt Me Me A94 Me OMe n-Pr Me A95 Me OEt Me Me A95 Me OMe n-Pr Me A97 Me OEt Me Me A97 Et OMe n-Pr Me H Et OEt Me Me H Et OMe n-Pr Me A13 Et OEt Me Me A13 Et OMe n-Pr Me A14 Et OEt Me Me A14 Et OMe n-Pr Me A16 Et OEt Me Me A16 Et OMe n-Pr Me A35 Et OEt Me Me A35 Et OMe n-Pr Me A38 Et OEt Me Me A38 Et OMe n-Pr Me A39 Et OEt Me Me A39 Et OMe n-Pr Me A40 Et OEt Me Me A40 Et OMe n-Pr Me A41 Et OEt Me Me A41 Et OMe n-Pr Me A73 Et OEt Me Me A73 Et OMe n-Pr Me A74 Et OEt Me Me A74 Et OMe n-Pr Me A75 Et OEt Me Me A75 Et OMe n-Pr Me A81 Et OEt Me Me A81 Et OMe n-Pr Me A82 Et OEt Me Me A82 Me OEt Et Me H Me OMe Me Et H Me OEt Et Me A13 Me OMe Me Et A13 Me OEt Et Me A14 Me OMe Me Et A14 Me OEt Et Me A16 Me OMe Me Et A16 Me OEt Et Me A35 Me OMe Me Et A35 Me OEt Et Me A38 Me OMe Me Et A38 Me OEt Et Me A39 Me OMe Me Et A39 Me OEt Et Me A40 Me OMe Me Et A40 Me OEt Et Me A41 Me OMe Me Et A41 Me OEt Et Me A73 Me OMe Me Et A73 Me OEt Et Me A74 Me OMe Me Et A74 Me OEt Et Me A75 Me OMe Me Et A75 Me OEt Et Me A81 Me OMe Me Et A81 Me OEt Et Me A82 Me OMe Me Et A82 Me OEt Et Me A83 Me OMe Me Et A83 Me OEt Et Me A84 Me OMe Me Et A84 Me OEt Et Me A85 Me OMe Me Et A85 Me OEt Et Me A86 Me OMe Me Et A86 Me OEt Et Me A87 Me OMe Me Et A87 Me OEt Et Me A91 Me OMe Me Et A91 Me OEt Et Me A92 Me OMe Me Et A92 Me OEt Et Me A93 Me OMe Me Et A93 Me OEt Et Me A94 Me OMe Me Et A94 Me OEt Et Me A95 Me OMe Me Et A95 Me OEt Et Me A97 Me OMe Me Et A97 Et OEt Et Me H Et OMe Me Et H Et OEt Et Me A13 Et OMe Me Et A13 Et OEt Et Me A14 Et OMe Me Et A14 Et OEt Et Me A16 Et OMe Me Et A16 Et OEt Et Me A35 Et OMe Me Et A35 Et OEt Et Me A38 Et OMe Me Et A38 Et OEt Et Me A39 Et OMe Me Et A39 Et OEt Et Me A40 Et OMe Me Et A40 Et OEt Et Me A41 Et OMe Me Et A41 Et OEt Et Me A73 Et OMe Me Et A73 Et OEt Et Me A74 Et OMe Me Et A74 Et OEt Et Me A75 Et OMe Me Et A75 Et OEt Et Me A81 Et OMe Me Et A81 Et OEt Et Me A82 Et OMe Me Et A82 Et OMe Me Me A83 Et OMe Et Me A83 Et OMe Me Me A84 Et OMe Et Me A84 Et OMe Me Me A85 Et OMe Et Me A85 Et OMe Me Me A86 Et OMe Et Me A86 Et OMe Me Me A87 Et OMe Et Me A87 Et OMe Me Me A91 Et OMe Et Me A91 Et OMe Me Me A92 Et OMe Et Me A92 Et OMe Me Me A93 Et OMe Et Me A93 Et OMe Me Me A94 Et OMe Et Me A94 Et OMe Me Me A95 Et OMe Et Me A95 Et OMe Me Me A97 Et OMe Et Me A97 Et OMe n-Pr Me A83 Et OEt Me Me A83 Et OMe n-Pr Me A84 Et OEt Me Me A84 Et OMe n-Pr Me A85 Et OEt Me Me A85 Et OMe n-Pr Me A86 Et OEt Me Me A86 Et OMe n-Pr Me A87 Et OEt Me Me A87 Et OMe n-Pr Me A91 Et OEt Me Me A91 Et OMe n-Pr Me A92 Et OEt Me Me A92 Et OMe n-Pr Me A93 Et OEt Me Me A93 Et OMe n-Pr Me A94 Et OEt Me Me A94 Et OMe n-Pr Me A95 Et OEt Me Me A95 Et OMe n-Pr Me A97 Et OEt Me Me A97 Et OEt Et Me A83 Et OMe Me Et A83 Et OEt Et Me A84 Et OMe Me Et A84 Et OEt Et Me A85 Et OMe Me Et A85 Et OEt Et Me A86 Et OMe Me Et A86 Et OEt Et Me A87 Et OMe Me Et A87 Et OEt Et Me A91 Et OMe Me Et A91 Et OEt Et Me A92 Et OMe Me Et A92 Et OEt Et Me A93 Et OMe Me Et A93 Et OEt Et Me A94 Et OMe Me Et A94 Et OEt Et Me A95 Et OMe Me Et A95 Et OEt Et Me A97 Et OMe Me Et A97

TABLE 4

R⁶ Z^(a) Z^(c) Z^(e) A R⁶ Z^(a) Z^(c) Z^(e) A Me Me Me OCH₂CF₃ H Me Me Et OCH₂CF₃ H Me Et Et OCH₂CF₃ H Me Me n-Pr OCH₂CF₃ H Me Me Me OCF₃ H Me Me Et OCF₃ H Me Et Et OCF₃ H Me Me n-Pr OCF₃ H Me Me Me OCF₂H H Me Me Et OCF₂H H Me Et Et OCF₂H H Me Me n-Pr OCF₂H H Me Me Me OCF₂Cl H Me Me Et OCF₂Cl H Me Et Et OCF₂Cl H Me Me n-Pr OCF₂Cl H Me Me Me OCF₂Br H Me Me Et OCF₂Br H Me Et Et OCF₂Br H Me Me n-Pr OCF₂Br H Me Me Me O(D1-32a) H Me Et Et O(D1-32a) H Me Me Me O(D1-32b-2) H Me Et Et O(D1-32b-2) H Me Me Me O(D1-32b-3) H Me Et Et O(D1-32b-3) H Me Me Me O(D1-32b-4) H Me Et Et O(D1-32b-4) H Me Me Me O(D1-32b-5) H Me Et Et O(D1-32b-5) H Me Me Me O(D1-33a) H Me Me Me O(D1-33a) H Me Me Me O(D1-33b-1) H Me Me Me O(D1-33b-1) H Me Me Me O(D1-33b-2) H Me Me Me O(D1-33b-2) H Me Me Me O(D1-33b-3) H Me Me Me O(D1-33b-3) H Me Me Me O(D1-33b-4) H Me Me Me O(D1-33b-4) H Me OMe Me Ph H Me OMe Et Ph H Me OMe Me Ph A39 Me OMe Et Ph A39 Me OMe Me Ph A40 Me OMe Et Ph A40 Me OMe Me Ph A41 Me OMe Et Ph A41 Me OMe Me D1-108b-4 H Me OMe Et D1-108b-4 H Me OMe Me D1-108b-4 A39 Me OMe Et D1-108b-4 A39 Me OMe Me D1-108b-4 A40 Me OMe Et D1-108b-4 A40 Me OMe Me D1-108b-4 A41 Me OMe Et D1-108b-4 A41 Me OMe Me D1-108b-4 A74 Me OMe Et D1-108b-4 A74 Me OMe Me D1-108b-4 A75 Me OMe Et D1-108b-4 A75 Me OMe Me D1-108b-4 A84 Me OMe Et D1-108b-4 A84 Me OMe Me D1-108b-4 A85 Me OMe Et D1-108b-4 A85 Me OMe Me D1-108b-4 A86 Me OMe Et D1-108b-4 A86 Me OMe Me D1-108b-4 A87 Me OMe Et D1-108b-4 A87 Me OMe Me D1-108b-8 H Me OMe Et D1-108b-8 H Me OMe Me D1-108b-8 A39 Me OMe Et D1-108b-8 A39 Me OMe Me D1-108b-8 A40 Me OMe Et D1-108b-8 A40 Me OMe Me D1-108b-8 A41 Me OMe Et D1-108b-8 A41 Me OMe Me D1-108b-8 A74 Me OMe Et D1-108b-8 A74 Me OMe Me D1-108b-8 A75 Me OMe Et D1-108b-8 A75 Me OMe Me D1-108b-8 A84 Me OMe Et D1-108b-8 A84 Me OMe Me D1-108b-8 A85 Me OMe Et D1-108b-8 A85 Me OMe Me D1-108b-8 A86 Me OMe Et D1-108b-8 A86 Me OMe Me D1-108b-8 A87 Me OMe Et D1-108b-8 A87 Me OMe Me Br H Me OMe Et Br H Me SMe Me Me H Me SMe Et Me H c-Pr OMe Me Me H c-Pr OMe Et Me H c-Pr OMe Me Me A12 c-Pr OMe Et Me A12 c-Pr OMe Me Me A13 c-Pr OMe Et Me A13 c-Pr OMe Me Me A74 c-Pr OMe Et Me A74 c-Bu OMe Me Me H c-Bu OMe Et Me H c-Bu OMe Me Me A12 c-Bu OMe Et Me A12 c-Bu OMe Me Me A13 c-Bu OMe Et Me A13 c-Bu OMe Me Me A74 c-Bu OMe Et Me A74 c-Pen OMe Me Me H c-Pen OMe Et Me H c-Pen OMe Me Me A12 c-Pen OMe Et Me A12 c-Pen OMe Me Me A13 c-Pen OMe Et Me A13 c-Pen OMe Me Me A74 c-Pen OMe Et Me A74 c-Hex OMe Me Me H c-Hex OMe Et Me H Me OMe n-Pr Ph H Me OEt Me Ph H Me OMe n-Pr Ph A39 Me OEt Me Ph A39 Me OMe n-Pr Ph A40 Me OEt Me Ph A40 Me OMe n-Pr Ph A41 Me OEt Me Ph A41 Me OMe n-Pr D1-108b-4 H Me OEt Me D1-108b-4 H Me OMe n-Pr D1-108b-4 A39 Me OEt Me D1-108b-4 A39 Me OMe n-Pr D1-108b-4 A40 Me OEt Me D1-108b-4 A40 Me OMe n-Pr D1-108b-4 A41 Me OEt Me D1-108b-4 A41 Me OMe n-Pr D1-108b-4 A74 Me OEt Me D1-108b-4 A74 Me OMe n-Pr D1-108b-4 A75 Me OEt Me D1-108b-4 A75 Me OMe n-Pr D1-108b-4 A84 Me OEt Me D1-108b-4 A84 Me OMe n-Pr D1-108b-4 A85 Me OEt Me D1-108b-4 A85 Me OMe n-Pr D1-108b-4 A86 Me OEt Me D1-108b-4 A86 Me OMe n-Pr D1-108b-4 A87 Me OEt Me D1-108b-4 A87 Me OMe n-Pr D1-108b-8 H Me OEt Me D1-108b-8 H Me OMe n-Pr D1-108b-8 A39 Me OEt Me D1-108b-8 A39 Me OMe n-Pr D1-108b-8 A40 Me OEt Me D1-108b-8 A40 Me OMe n-Pr D1-108b-8 A41 Me OEt Me D1-108b-8 A41 Me OMe n-Pr D1-108b-8 A74 Me OEt Me D1-108b-8 A74 Me OMe n-Pr D1-108b-8 A75 Me OEt Me D1-108b-8 A75 Me OMe n-Pr D1-108b-8 A84 Me OEt Me D1-108b-8 A84 Me OMe n-Pr D1-108b-8 A85 Me OEt Me D1-108b-8 A85 Me OMe n-Pr D1-108b-8 A86 Me OEt Me D1-108b-8 A86 Me OMe n-Pr D1-108b-8 A87 Me OEt Me D1-108b-8 A87 Me OMe n-Pr Br H Me OEt Me Br H Me SMe n-Pr Me H Me SEt Me Me H c-Pr OMe n-Pr Me H c-Pr OEt Me Me H c-Pr OMe n-Pr Me A12 c-Pr OEt Me Me A12 c-Pr OMe n-Pr Me A13 c-Pr OEt Me Me A13 c-Pr OMe n-Pr Me A74 c-Pr OEt Me Me A74 c-Bu OMe n-Pr Me H c-Bu OEt Me Me H c-Bu OMe n-Pr Me A12 c-Bu OEt Me Me A12 c-Bu OMe n-Pr Me A13 c-Bu OEt Me Me A13 c-Bu OMe n-Pr Me A74 c-Bu OEt Me Me A74 c-Pen OMe n-Pr Me H c-Pen OEt Me Me H c-Pen OMe n-Pr Me A12 c-Pen OEt Me Me A12 c-Pen OMe n-Pr Me A13 c-Pen OEt Me Me A13 c-Pen OMe n-Pr Me A74 c-Pen OEt Me Me A74 c-Hex OMe n-Pr Me H c-Hex OEt Me Me H Me OEt Et Ph H c-Hex OMe Me Me A12 Me OEt Et Ph A39 c-Hex OMe Me Me A13 Me OEt Et Ph A40 c-Hex OMe Me Me A74 Me OEt Et Ph A41 Me OMe Me Me H Me OEt Et D1-108b-4 H Me OMe Br Me H Me OEt Et D1-108b-4 A39 Me Me Me Me H Me OEt Et D1-108b-4 A40 c-Hex OMe n-Pr Me A12 Me OEt Et D1-108b-4 A41 c-Hex OMe n-Pr Me A13 Me OEt Et D1-108b-4 A74 c-Hex OMe n-Pr Me A74 Me OEt Et D1-108b-4 A75 Me OMe n-Pr Me H Me OEt Et D1-108b-4 A84 Me OMe n-Pr Me H Me OEt Et D1-108b-4 A85 Me Me n-Pr Me H Me OEt Et D1-108b-4 A86 Me OMe F Br H Me OEt Et D1-108b-4 A87 Me OMe F Ph H Me OEt Et D1-108b-8 H Me OMe F Me H Me OEt Et D1-108b-8 A39 c-Hex OMe Et Me A12 Me OEt Et D1-108b-8 A40 c-Hex OMe Et Me A13 Me OEt Et D1-108b-8 A41 c-Hex OMe Et Me A74 Me OEt Et D1-108b-8 A74 Me OMe Et Me H Me OEt Et D1-108b-8 A75 Me OMe Et Me H Me OEt Et D1-108b-8 A84 Me Me Et Me H Me OEt Et D1-108b-8 A85 c-Hex OEt Me Me A12 Me OEt Et D1-108b-8 A86 c-Hex OEt Me Me A13 Me OEt Et D1-108b-8 A87 c-Hex OEt Me Me A74 Me OEt Et Br H Me OMe Et Me H Me OEt Et Me H Me OMe Et Me H c-Pr OEt Et Me H Me Et Et Me H c-Pr OEt Et Me A12 Me OEt F Br H c-Pr OEt Et Me A13 Me OEt F Ph H c-Pr OEt Et Me A74 Me OEt F Me H c-Bu OEt Et Me H c-Pen OEt Et Me A13 c-Bu OEt Et Me A12 c-Pen OEt Et Me A74 c-Bu OEt Et Me A13 c-Hex OEt Et Me H c-Bu OEt Et Me A74 c-Hex OEt Et Me A12 c-Pen OEt Et Me H c-Hex OEt Et Me A13 c-Pen OEt Et Me A12 c-Hex OEt Et Me A74 Me OMe F Br H Me OEt F Br H Me OMe F Ph H Me OEt F Ph H Me OMe F Me H Me OEt F Me H

The compound of the present invention can be used in both treatment methods of soil application and foliage application under flooding as a herbicide for paddy fields. Examples of paddy field weeds may include Potamogetonaceae weeds represented by Potamogeton distinctus; Alismataceae weeds represented by Alisma canaliculatum, Sagittaria pygmaea, and Sagittaria trifolia; Gramineae weeds represented by Leptochloa chinensis, Echinochloa crus-galli, Echinochloa oryzicola, Homalocenchrus japonocus, and Paspalum distichum; Cyperaceae weeds represented by Eleocharis kuroguwai, Scirpus juncoides, Scirpus nipponicus, Cyperus serotinus, Cyperus difformis, and Cyperus hakonensis; Lemnaceae weeds represented by Spirodela polyrhiza and Lemna paucicostata; Commelinaceae weeds represented by Murdannia keisak; Pontederiaceae weeds represented by Monochoria korsakowii and Monochoria vaginalis; Elatinaceae weeds represented by Elatine triandra; Lythraceae weeds represented by Ammannia multiflora and Rotala indica; Oenotheraceae weeds represented by Lidwigia epilobioides; Scrophulariaceae weeds represented by Dopatrium junceum, Gratiola japonica, Limnophila sessilifolia, Lindernia pyxidaria, and Lindernia dubia; Leguminosae weeds such as Aeschynomene indica, and Compositae weeds represented by, Bidens frondosa and Bidens tripartita.

The compound of the present invention can also be used in any treatment methods of soil treatment, soil incorporation treatment, and foliage treatment as a herbicide for farmlands and orchards. Examples of the farmland weeds may include broad-leaved weeds such as Solanaceae weeds represented by Solanum nigrum and Datura stramonium; Geraniaceae weeds represented by Granium carolinianum; Malvaceae weeds represented by Abutilon theophrasti and Sida spinosa; Convolvulaceae weeds represented by Ipomoea spps such as Ipomoea purpurea and Calystegia spps; Amaranthaceae weeds represented by Amaranthus lividus and Amaranthus retroflexus; Compositae weeds represented by Xanthium pensylvanicum, Ambrosia artemisiaefolia, Helianthus annuus, Galinsoga ciliata, Cirsium arvense, Senecio vulgaris, and Erigeron annus; Cruciferae weeds represented by Rorippa indica, Sinapis arvensis, and Capsella Bursapastoris; Polygonaceae weeds represented by Polygonum Blumei and Polygonum convolvulus; Portulacaceae weeds represented by Portulaca oleracea; Chenopodiaceae weeds represented by Chenopodium album, Chenopodium ficifolium, and Kochia scoparia; Caryophyllaceae weeds represented by Stellaria media; Scrophulariaceae weeds represented by Veronica persica; Commelinaceae weeds represented by Commelina communis; Labiatae weeds represented by Lamium amplexicaule and Lamium purpureum; Euphorbiaceae weeds represented by Euphorbia supina and Euphorbia maculata; Rubiaceae weeds represented by Galium spurium and Rubia akane; Violaceae weeds represented by Viola mandshurica; Leguminosae weeds represented by Sesbania exaltata and Cassia obtusifolia; and Oxsaldaseae represented by Oxsalis courniculata; Graminaceous weeds represented by Sorgham bicolor, Panicum dichotomiflorum, Sorghum halepense, Echinochloa crus-galli var. Crus-galli, Echinochloa crus-galli var. Praticola, Echinochloa utilis, Digitaria ciliaris, Avena fatua, Alopecurus myosuroides, Eleusine indica, Setaria viridis, Setaria faberi, and Alopecurus aegualis; and Cyperaceous weeds represented by Cyperus rotundus and Cyperus esculentus.

The compound of the present invention can be used in any application methods of soil application, soil incorporation application, and foliage application in non-agricultural lands such as turfs, play grounds, open grounds, side of roads, and line ends other than the agricultural and horticultural fields such as paddy fields, farmlands, and orchards. As weeds in these non-agricultural lands, the following examples of the weeds are exemplified in addition to the weeds described in farmlands and orchards. The examples of the weed may include Poa annua, Taraxacum officinale, Conyza sumatrensis, Cardamine flexuosa, Trifolium repens, Hydrocotyle sibthorpioides, Plantago asiatica, Cyperus brevifolius, Kyllinga brevifolia, and Equisetum arvense.

The compound of the present invention may be applied in a mixed state with other herbicides, various insecticides, bactericides, plant growth regulators, or synergists at the time of herbicide formulation or spray, if necessary.

In particular, by applying the herbicide in a mixed state with another herbicide, reduction in cost due to reduction in an application amount, expansion in herbicidal spectrum due to synergistic action of mixed herbicides, and a higher herbicidal effect can be expected. At this time, a combination of a plurality of known herbicides at the same time is also possible.

Examples of the preferable herbicide used by mixing with the compound of the present invention may include acetochlor/general name, acifluorfen/general name, aclonifen/general name, alachlor/general name, alloxydim/general name, alloxydim-sodium/general name, ametryn/general name, amicarbazone/general name, amidosulfuron/general name, aminocyclopirachlor/general name, aminocyclopirachlor-salts and esters, aminopyralid/general name, aminopyralid-salts and esters, amiprophos-methyl/general name, amitrol/general name, anilofos/general name, asulam/general name, atrazine/general name, azafenidin/general name, azimsulfuron/general name, beflubutamid/general name, benazolin-ethyl/general name, bencarbazone/general name, benfluralin (benefin)/general name, benfuresate/general name, bensulfuron-methyl/general name, bensulide/general name, bentazone/general name, bentazone-sodium/general name, bentazone-salts, benthiocarb/general name, benzfendizone/general name, benzobicyclon/general name, benzofenap/general name, bialaphos/general name, bialaphos-sodium/general name, bicyclopyrone/general name, bifenox/general name, bispyribac/general name, bispyribac-sodium/general name, bromacil/general name, bromobutide/general name, bromofenoxim/general name, bromoxynil/general name, bromoxynil-salts and esters, butachlor/general name, butafenacil/general name, butamifos/general name, butenachlor/general name, butralin/general name, butroxydim/general name, butylate/general name, cafenstrole/general name, carbetamide/general name, carfentrazone-ethyl, chlomethoxyfen/general name, chlomethoxynil/general name, chloramben/general name, chloramben-salts and esters, chloransulam-methyl/general name, chlorflurenol-methyl/general name, chloridazon/general name, chlorimuron-ethyl/general name, chlorobromuron/general name, chlorotoluron/general name, chloroxuron/general name, chlorphtalim/general name, chlorpropham/general name, chlorpropham/general name, chlorsulfuron/general name, chlorthal-dimethyl/general name, chlorthiamid/general name, cinidon-ethyl/general name, cinmethylin/general name, cinosulfuron/general name, clethodim/general name, clodinafop/general name, clodinafop-propargyl/general name, clomazone/general name, clomeprop/general name, clopyralid/general name, clopyralid-salts and esters, CNP/general name, cumyluron/general name, cyanazin/general name, cycloate/general name, cyclopyrimorate/general name (SW-065/test name), cyclosulfamuron/general name, cycloxydim/general name, cyhalofop-butyl/general name, DAH-500/test name, dalapon/general name, dazomet/general name, desmedipham/general name, desmetryn/general name, dicamba/general name, dicamba-salts and esters, dichlobenil/general name, diclofop/general name, diclofop-methyl/general name, dichlorprop/general name, dichlorprop-salts and esters, dichlorprop-P/general name, dichlorprop-P-salts and esters, diclosulam/general name, difenzoquat/general name, diflufenican/general name, diflufenzopyr/general name, diflufenzopyr-sodium/general name, dimepiperate/general name, dimethametryn/general name, dimethachlor/general name, dimethenamid/general name, dimethenamid-p/general name, dimethipin/general name, dinitramine/general name, dinoseb/general name, dinoterb/general name, DNOC/general name, diphenamid/general name, diquqt/general name, dithiopyl/general name, diuron/general name, DSMA/general name, dymron/general name, endothal/general name, EPTC/general name, esprocarb/general name, ethalfluralin/general name, ethametsulfuron-methyl/general name, ethofumesate/general name, etobenzanid/general name, ethoxysulfuron/general name, flazasulfuron/general name, fenoxaprop/general name, fenoxaprop-ethyl/general name, fenoxasulfone/general name, fenquionotrion/general name, fentrazamide/general name, flamprop/general name, flazasulfuron/general name, florasulam/general name, fluazifop/general name, fluazifop-butyl/general name, fluazolate/general name, flucarbazone-sodium/general name, flucetosulfuron/general name, flucloralin/general name, flufenacet/general name, flufenpyl-ethyl/general name, flumetsulam/general name, flumiclorac-pentyl/general name, flumioxazin/general name, fluometuron/general name, fluoroglycofen-ethyl/general name, flupyrsulfuron/general name, flupoxam/general name, flurenol/general name, fluridone/general name, flurochloridone/general name, fluroxypyr/general name, fluroxypyr-esters, flurprimidol/general name, flurtamone/general name, fluthiacet-methyl/general name, fomesafen/general name, foramsulfuron/general name, fosamine/general name, glufosinate/general name, glufosinate-ammonium/general name, glyphosate/general name, glyphosate-ammonium/general name, glyphosate-iso-propylammonium/general name, glyphosate-potassium/general name, glyphosate-sodium/general name, glyphosate-trimesium/general name, halauxifen/general name, halauxifen-salts and esters, halosafen/general name, halosulfuron/general name, halosulfuron-methyl/general name, haloxyfop/general name, haloxyfop-methyl/general name, hexazinone/general name, imazamethabenz-methyl/general name, imazamox/general name, imazapic/general name, imazapyr/general name, imazethapyr/general name, imazaquin/general name, imazosulfuron/general name, indanofan/general name, indaziflam/general name, iodosulfuron-methyl-sodium/general name, ioxynil octanoate/general name, ioxynil-salts and esters, ipfencarbazone/general name, isoproturon/general name, isouron/general name, isoxaben/general name, isoxaflutole/general name, karbutilate/general name, lactofen/general name, lenacil/general name, linuron/general name, maleic hydrazide/general name, MCPA/general name, MCPA-salts and esters, MCPB/general name, MCPB-salts and esters, mecoprop (MCPP)/general name, mecoprop-salts and esters, mecoprop-P (MCPP-P)/general name, mecoprop-P-salts and esters, mefenacet/general name, mefluidide/general name, mesosulfuron-methyl/general name, mesotrione/general name, metam/general name, metamifop/general name, metamitron/general name, metazachlor/general name, methabenzthiazuron/general name, metazosulfuron/general name, methiozolin/general name, methyl azide/general name, methyl bromide/general name, methyl dymron/general name, methyl iodide/general name, metobenzuron/general name, metolachlor/general name, metolachlor-S/general name, metosulam/general name, metribuzin/general name, metsulfuron-methyl/general name, metoxuron/general name, molinate/general name, monolinuron/general name, monosulfuron/general name, monosulfuron-methyl/general name, MSMA/general name, naproanilide/general name, napropamide/general name, naptalam/general name, naptalam-sodium/general name, neburon/general name, nicosulfuron/general name, norflurazon/general name, OK-701/test name, oleic acid/general name, orbencarb/general name, orthosulfamuron/general name, oryzalin/general name, oxadiargyl/general name, oxadiazon/general name, oxasulfuron/general name, oxaziclomefone/general name, oxyfluorfen/general name, paraquat/general name, pelargonic acid/general name, pendimethalin/general name, penoxsulam/general name, pentanochlor/general name, pentoxazone/general name, pethoxamid/general name, phenmedipham-ethyl/general name, picloram/general name, picloram-salts and esters, picolinafen/general name, pinoxaden/general name, piperophos/general name, pretilachlor/general name, primisulfuron-methyl/general name, prodiamine/general name, profluazol/general name, profoxydim/general name, prometon/general name, prometryn/general name, propachlor/general name, propanil/general name, propaquizafop/general name, propazin/general name, propham/general name, propisochlor/general name, propoxycarbazone-sodium/general name, propyrisulfuron/general name, propyzamide/general name, prosulfocarb/general name, prosulfuron/general name, pyraclonil/general name, pyraflufen-ethyl/general name, pyrasulfotole/general name, pyrazolynate/general name, pyrazosulfuron/general name, pyrazosulfuron-ethyl/general name, pyrazoxyfen/general name, pyribenzoxim/general name, pyributicarb/general name, pyridafol/general name, pyridate/general name, pyriftalid/general name, pyriminobac-methyl/general name, pyrimisulfan/general name, pyrithiobac-sodium/general name, pyroxasulfone/general name, pyroxsulam/general name, quinclorac/general name, quinmerac/general name, quinoclamine/general name, quizalofop/general name, quizalofop-ethyl/general name, quizalofop-tefuryl/general name, quizalofop-P/general name, quizalofop-P-ethyl/general name, quizalofop-P-tefuryl/general name, rimsulfuron/general name, saflufenacil/general name, sethoxydim/general name, siduron/general name, simazine/general name, simetryn/general name, SL-261/test name, sulcotrione/general name, sulfentrazone/general name, sulfometuron-methyl/general name, sulfosulfuron/general name, TCBA (2,3,6-TBA)/general name, 2,3,6-TBA-salts and esters, TCTP (chlorthal-dimethyl, tetrachlorothiophene)/general name, tebutam/general name, tebuthiuron/general name, tefuryltrione/general name, tembotrione/general name, tepraloxydim/general name, terbacil/general name, terbumeton/general name, terbuthylazine/general name, terbutryn/general name, tetrapion (flupropanate)/general name, thenylchlor/general name, thiazafluron/general name, thiazopyr/general name, thidiazimin/general name, thidiazuron/general name, thiencarbazone-methyl/general name, thifensulfuron-methyl/general name, tolpyralate/general name, topramezon/general name, tralkoxydim/general name, triafamone/general name, triallate/general name, triasulfuron/general name, triaziflam/general name, tribenuron-methyl/general name, triclopyr/general name, triclopyr-salts and esters, tridiphane/general name, trietazine/general name, trifludimoxadin/general name, trifloxysulfuron/general name, trifluralin/general name, triflusulfuron-methyl/general name, tritosulfuron/general name, 2,4-PA/general name, 2,4-PA-salts and esters, 2,4-DB/general name, and 2,4-DB-salts and esters. These components may be used singly or in combination of two or more of them. When these components are mixed, the ratio may be freely selected.

Examples of safeners may include AD-67, benoxacor/general name, cloquintocet-mexyl/general name, cyomerinil/general name, dichlormid/general name, dicyclonone/general name, cyprosulfamide/general name, diethorate/general name, DKA-24, dymron/general name, fenclorazole-ethyl/general name, fenclorim/general name, HEXM/general name, flurazole/general name, fluxofenim/general name, furilazole/general name, isoxadifen/general name, isoxadifen-ethyl/general name, MCPA, mecoprop/general name, mefenpyr/general name, mefenpyr-ethyl/general name, mefenpyr-diethyl/general name, mephenate/general name, MG-191, NA (Naphthalic anhydride), OM (Octamethylene-diamine), oxabetrinil/general name, PPG-1292, and R-29148. These components may be used singly or in combination of two or more of them. When these components are mixed, the ratio may be freely selected.

When the compound of the present invention is applied as the herbicide, the compound is usually mixed with an appropriate solid carrier or liquid carrier. Surfactants, penetrating agents, spreading agents, thickeners, antifreeze agents, binders, anti-caking agents, disintegrating agents and stabilizing agents can be further added, if desired. The herbicide can be applied to practical uses by any herbicide formulation of the herbicide form such as water-dispersible agents, emulsion agents, flowable agents, dry-flowable agents, liquid agents, powder agents, granule agents, or gel agents. From the viewpoint of power saving and improvement in safety, any of the herbicide formulation of the herbicide form can be supplied by encapsulating in a water-soluble package.

Examples of the solid carriers may include natural minerals such as quartz, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth; inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate and potassium chloride; and synthetic silicic acid and synthetic silicates.

Examples of the liquid carriers may include alcohols such as ethylene glycol, propylene glycol, and isopropanol (2-propanol); aromatic hydrocarbons such as xylene, alkylbenzenes, and alkylnaphthalenes; ethers such as butylcellosolve; ketones such as cyclohexanone; esters such as y-butyrolactone; acid amide such as N-methylpyrrolidone and N-octylpyrrolidone; vegetable oils such as soybean oil, rapeseed oil, cotton seed oil, and castor oil; and water.

These solid carriers and liquid carriers may be used singly or in combination of two or more of them.

Examples of the surfactant may include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene styrylphenyl ethers, polyoxyethylene-polyoxypropylene block copolymers, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters; anionic surfactants such as alkyl sulfates, alkylbenzene sulfonates, lignin sulfonates, alkyl sulfosuccinates, naphthalene sulfonate, alkylnaphthalene sulfonates, salts of formalin condensate of naphthalene sulfonic acid, salts of formalin condensate of alkylnaphthalene sulfonic acids, polyoxyethylene alkylaryl ether sulfates and phosphates, polyoxyethylene styrylphenyl ether sulfates and phosphates, polycarboxylates, and polystyrene sulfonates; cationic surfactants such as alkylamine salts and alkyl quaternary ammonium salts; and amphoteric surfactants such as amino acid-type surfactants and betaine-type surfactants.

The content of the surfactants is not particularly limited. Usually, the content is preferably in a range of 0.05 part by mass to 20 parts by mass relative to 100 parts by mass of the herbicide formulation of the present invention. These surfactants may be used singly or in combination of two or more of them.

The compound of the present invention may be applied in a mixed state with other herbicides, various insecticides, bactericides, plant growth regulators, or synergists at the time of herbicide formulation or spray, if necessary.

In particular, by applying the herbicide in a mixed state with another herbicide, reduction in cost due to reduction in an application amount, expansion in herbicidal spectrum due to synergistic action of mixed herbicides, and a higher herbicidal effect can be expected. At this time, a combination of a plurality of known herbicides at the same time is also possible.

Although the application amount of the compound of the present invention varies depending on an application stage, an application time, an application method, and a cultivated crop, the appropriate application amount is generally 0.005 kg to 50 kg per hectare (ha) as the amount of the active component.

The formulation examples of the herbicide formulations when the compound of the present invention is used will be described. However, the formulation examples of the present invention are not limited to these examples. Hereinafter, the term “part” in the formulation examples means part by mass.

Water-Dispersible Agent

Compound of the present invention 0.1 part to 80 parts  Solid carrier  5 parts to 98.9 parts Surfactant 1 part to 10 parts Others 0 part to 5 parts 

Examples of Others may include anti-caking agents and stabilizing agents.

Emulsion Agent

Compound of the present invention  0.1 part to 30 parts Liquid carrier 45 parts to 95 parts Surfactant 4.9 parts to 15 parts  Others   0 part to 10 parts

Examples of Others may include spreading agents and stabilizing agents.

Flowable Agent

Compound of the present invention 0.1 part to 70 parts  Liquid carrier  15 parts to 98.89 parts Surfactant 1 part to 12 parts Others 0.01 part to 30 parts  

Examples of Others may include antifreeze agents and thickeners.

Dry Flowable Agent

Compound of the present invention 0.1 part to 90 parts  Solid carrier  0 part to 98.9 parts Surfactant 1 part to 20 parts Others 0 part to 10 parts

Examples of Others may include binders and stabilizing agents.

Liquid Agent

Compound of the present invention 0.01 part to 70 parts   Liquid carrier  20 parts to 99.99 parts Others 0 part to 10 parts

Examples of Others may include antifreeze agents and spreading agents.

Granule Agent

Compound of the present invention 0.01 part to 80 parts   Solid carrier  10 parts to 99.99 parts Others 0 part to 10 parts

Examples of Others may include binders and stabilizing agents.

Powder Agent

Compound of the present invention 0.01 part to 30 parts   Solid carrier  65 parts to 99.99 parts Others 0 part to 10 parts

Examples of Others may include anti-drift agent and stabilizing agents.

When the formulation is used, the formulation is applied as it is or by diluting the formulation to 1 to 10000 times with water.

Herbicide Formulation Example

Examples of agricultural chemical formulation containing the compound of the present invention as the active component will be described. The present invention, however, is not limited to these examples. Hereinafter, the term “part” in the formulation examples means part by mass.

[Formulation Example 1] Water-Dispersible Agent

Compound of the present invention No. 1-001 20 parts Pyrophyllite 76 parts Sorpol 5039  2 parts (Anionic surfactant: manufactured by TOHO Chemical Industry Co., Ltd., trade name) CARPLEX #80  2 parts (Synthetic hydrated silicic acid: Shionogi & Co., Ltd., trade name)

The above components are homogeneously mixed and pulverized to form the water-dispersible agent.

[Formulation Example 2] Emulsion Agent

Compound of the present invention No. 1-001  5 parts Xylene 75 parts N-methylpyrrolidone 15 parts Sorpol 2680  5 parts (Anionic surfactant: manufactured by TOHO Chemical Industry Co., Ltd., trade name)

The above components are homogeneously mixed to form the emulsion agent.

[Formulation Example 3] Flowable Agent

Compound of the present invention No. 1-001 25 parts Agrisol S-710 10 parts (Nonionic surfactant: Kao Corporation, trade name) Lunox 1000C 0.5 part   (Anionic surfactant: manufactured by TOHO Chemical Industry Co., Ltd., trade name) Xanthan gum 0.02 part   Water 64.48 parts  

The above components are homogeneously mixed and thereafter the mixture was wet-pulverized to form the flowable agent.

[Formulation Example 4] Dry Flowable Agent

Compound of the present invention No. 1-001 75 parts HITENOL NE-15  5 parts (Anionic surfactant: manufactured by DKS Co. Ltd., trade name) Vanillex N 10 parts (Anionic surfactant: manufactured by NIPPON PAPER INDUSTRIES CO., LTD., trade name) CARPLEX #80 10 parts (Synthetic hydrated silicic acid: Shionogi & Co., Ltd., trade name)

The above components are homogeneously mixed and pulverized. Thereafter, a small amount of water was added to the mixture and the resultant mixture was stirred, mixed, and kneaded. The obtained mixture was granulated with an extruding-type granulator. The resultant granules are dried to form the dry flowable agent.

[Formulation Example 5] Granular Agent

Compound of the present invention No. 1-001  1 part Bentonite 55 parts Talc 44 parts

The above components are homogeneously mixed and pulverized. Thereafter, a small amount of water was added to the mixture and the resultant mixture was stirred, mixed, and kneaded. The obtained mixture was granulated with an extruding-type granulator. The resultant granules are dried to form the granular agent.

Examples

Hereinafter, in the herbicide of the present invention, the present invention will be further described in detail by specifically describing Synthesis Examples and Test Examples of the ketone or oxime compound of Formula (1) used as the active component as Examples. The present invention, however, is not limited to these Examples.

As a medium pressure preparative liquid chromatography described in Synthesis Examples, medium pressure preparative apparatus; YFLC-Wprep (flow rate: 18 ml/min, 40 μm silica gel packed column) manufactured by Yamazen Corporation was used.

Discaver manufactured by CEM Co., Ltd. was used as a microwave synthesizing apparatus, and a sealed container dedicated for the apparatus was used as a reaction container.

10AVP System manufactured by Shimadzu Corporation was used as a high performance liquid chromatography.

The chemical shift values of proton nuclear magnetic resonance in Examples were measured at 300 MHz using Me₄Si (tetramethylsilane) as a reference substance. Solvents used in measurement are described in Synthesis Examples below. The symbols of the chemical shift values of proton nuclear magnetic resonance in Examples have the following meanings.

s: singlet, brs: broad singlet, d: doublet, t: triplet, and m: multiplet

Synthesis Examples Synthesis Example 1: Production of 2-mesityl-3-methoxy-5-{2-(methoxyimino)propyl}cyclopent-2-enone (Compound No. 1-001)

The mixed solution of 0.5 g of 2-mesityl-3-methoxycyclopent-2-enone synthesized by the method described in WO 2010/000773 Pamphlet and 10 ml of tetrahydrofuran was cooled to −78° C. under a nitrogen atmosphere, and thereafter 2.3 ml of lithium diisopropylamide (the mixed solution of about 1.5 mol/L of n-hexane and tetrahydrofuran, manufactured by KANTO CHEMICAL CO., INC.) was added dropwise. After completion of the dropwise addition, the reaction mixture was stirred at the same temperature for 30 minutes. After completion of the stirring, 0.34 g of l-chloropropan-2-one O-methyl oxime was added to the reaction mixture. After completion of the addition, the reaction solution was stirred at −78° C. for 20 minutes. Thereafter the temperature of the reaction solution was raised to room temperature and the reaction solution was stirred at the same temperature for 15 hours. After completion of the reaction, the reaction mixture was added to ice water and the resultant mixture was extracted with 20 ml of ethyl acetate. The obtained organic phase was washed with water and dehydrated and dried with anhydrous sodium sulfate. Thereafter, the solvent was distilled away under reduced pressure. The obtained residue was purified with medium pressure preparative liquid chromatography eluting the residue with n-hexane-ethyl acetate [1:1 (volume ratio, the same applies hereinafter)] to give 76 mg of the target compound as a white solid.

Melting point 92° C. to 98° C.

Synthesis Example 2: Production of 3-hydroxy-2-mesityl-5-(2-oxopropyl)cyclopent-2-enone (Compound No. 2-001)

To the mixed solution of 60 mg of 2-mesityl-3-methoxy-5-{2-(methoxyimino)propyl}cyclopent-2-enone and 1 ml of acetone, 1 ml of 2 M hydrochloric acid aqueous solution was added. After completion of the addition, the reaction mixture was stirred at 50° C. for 4 hours. After completion of the reaction, 5 ml of ethyl acetate was added to the reaction mixture to take out the organic phase. The obtained organic phase was washed with water and dehydrated and dried with anhydrous sodium sulfate. Thereafter, the solvent was distilled away under reduced pressure to give 56 mg of the target compound as a white solid.

Melting point; 183° C. to 185° C.

Synthesis Example 3: Production of 3-hydroxy-2-mesityl-5-({2-(methoxyimino)propyl}cyclopent-2-enone (Compound No. 1-002)

To the mixed solution of 50 mg of 3-hydroxy-2-mesityl-5-(2-oxopropyl)cyclopent-2-enone, 2 ml of methanol, and 1 ml of water, 24 mg of O-methylhydroxylamine hydrochloride was added. After completion of the addition, the reaction mixture was stirred at 50° C. for 1 hour. After completion of the reaction, the solvent was distilled away from the reaction mixture under reduced pressure. After 10 ml of ethyl acetate was added to the obtained residue, the mixture was washed with water. The obtained organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and then anhydrous sodium sulfate in this order and the solvent was distilled away under reduced pressure to give 31 mg of the target compound as a white solid.

Melting point; 170° C. to 173° C.

Synthesis Example 4: Production of 2-mesityl-4-{2-(methoxyimino)propyl}-3-oxocyclopent-1-en-1-yl pivalate (Compound No. 1-004)

To the mixed solution of 150 mg of 3-hydroxy-2-mesityl-5-{2-(methoxyimino)propyl}cyclopent-2-enone and 5 ml of dichloromethane, 139 mg of triethylamine, 6 mg of 4-dimethylaminopyridine, and 186 mg of pivalic anhydride were sequentially added. After completion of the addition, the reaction mixture was stirred at room temperature for 15 hours. After completion of the reaction, 5 ml of water was added to the reaction mixture and the resultant mixture was extracted with 10 ml of chloroform. The obtained organic phase was dehydrated and dried with anhydrous sodium sulfate, and thereafter the solvent was distilled away under reduced pressure. After the solvent was distilled away, the obtained residue was purified with medium pressure preparative liquid chromatography eluting the residue with hexane-ethyl acetate (2:1) to give 150 mg of the target compound as a colorless oily product.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 6.85-6.81 (m, 2H), 3.87-3.82 (m, 3H), 3.70-2.18 (m, 8H), 2.15-1.78 (m, 9H), 1.08 and 1.06 (s, 9H).

Synthesis Example 5: Production of 2-(4-bromo-2-methoxy-6-methylphenyl)-3-hydroxy-5-(2-oxopropyl)cyclopent-2-enone (Compound No. 7-027) Process 1: Production of 5-bromo-2-iodo-1-methoxy-3-methylbenzene

The mixed solution of 15.7 g of 4-bromo-2-methoxy-6-methylaniline synthesized by the method described in WO 2005/028479 Pamphlet, 130 ml of concentrated hydrochloric acid, and 130 ml of water was cooled to 0° C. To the mixed solution, 5.5 g of sodium nitrite was added, while maintaining the temperature at 5° C. or lower and the resultant reaction solution was further stirred for 30 minutes. Subsequently, the mixed solution of 13.3 g of potassium iodide and 65 ml of water was added to the reaction solution while maintaining the temperature at 5° C. or lower and thereafter the resultant reaction solution was stirred at room temperature for 15 hours. After completion of the reaction, the reaction solution was extracted with 200 ml of 1,2-dichloroethane. The obtained organic phase was washed with 200 ml of 1 mol/L of a sodium hydroxide aqueous solution, 200 ml of 1 mol/L of a sodium sulfite aqueous solution, 200 ml of 1 mol/L of a hydrochloric acid aqueous solution, and 200 ml of a saturated sodium hydrogencarbonate solution in this order. Subsequently, the obtained organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and then anhydrous sodium sulfate in this order and the solvent was distilled away under reduced pressure. The obtained residue was purified with medium pressure preparative liquid chromatography eluting the residue with n-hexane-ethyl acetate (10:1) to give 10.3 g of the target compound as a brown solid.

Melting point; 72° C. to 75° C.

Process 2: Production of (4-bromo-2-methoxy-6-methylphenyl)(furan-2-yl)methanol

The mixed solution of 5 g of 5-bromo-2-iodo-1-methoxy-3-methylbenzene and 50 ml of tetrahydrofuran was cooled to −70° C. under a nitrogen atmosphere. To the mixed solution, 8.1 ml of an isopropylmagnesium chloride-lithium chloride complex (about 1 mol/L of a tetrahydrofuran solution, manufactured by Tokyo Chemical Industry Co., Ltd.) and then 4.6 ml of isopropyl magnesium chloride (about 1 mol/L of a tetrahydrofuran solution, manufactured by Tokyo Chemical Industry Co., Ltd.) were sequentially added and the resultant mixture was stirred for 30 minutes. Thereafter, the mixed solution of 2.2 g of furfural and 20 ml of tetrahydrofuran was added to the mixture. After completion of the addition, the temperature of the resultant reaction solution was raised to room temperature and the reaction solution was stirred at the same temperature for 15 hours. After completion of the reaction, 50 ml of saturated ammonium chloride aqueous solution was added to the reaction solution and the solvent was distilled away under reduced pressure until the amount of the solvent reached to a half amount. The obtained residue was extracted with 30 ml of ethyl acetate, dehydrated and dried with saturated sodium chloride aqueous solution and then anhydrous sodium sulfate in this order, followed by distilling away the solvent under reduced pressure. The obtained residue was purified with medium pressure preparative liquid chromatography eluting the residue with n-hexane-ethyl acetate (gradient from 20:1 to 10:1) to give 4.6 g of the target compound as a yellow oily product.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.38-7.34 (m, 1H), 7.00 (brs, 1H), 6.97 (brs, 1H), 6.37-6.20 (m, 1H), 6.03-5.92 (m, 2H), 3.83 (s, 3H), 4.21 (d, J=10.8 Hz, 1H), 2.31 (s, 3H).

Process 3: Production of 5-(4-bromo-2-methoxy-6-methylphenyl)-4-hydroxycyclopent-2-enone

The mixed solution of 2.6 g of polyphosphoric acid, 10 ml of acetone, and 4 ml of water was added to the mixed solution of 4.6 g of (4-bromo-2-methoxy-6-methylphenyl)(furan-2-yl)methanol, 35 ml of acetone, and 10 ml of water and the resultant reaction mixture was stirred at 55° C. for 1 hour. After completion of the reaction, the solvent was distilled away under reduced pressure until the volume of the reaction mixture reached a half volume. To the obtained residue, 30 ml of water was added and the resultant mixture was extracted with 30 ml of ethyl acetate. The obtained organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and then anhydrous sodium sulfate in this order and the solvent was distilled away under reduced pressure. The obtained residue was purified with medium pressure preparative liquid chromatography eluting the residue with n-hexane-ethyl acetate (gradient from 4:1 to 1:2) to give 3.1 g of the target compound as a brown oily product.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.52-7.46 (m, 1H), 7.02 (brs, 1H), 6.84 (brs, 1H), 6.36-6.28 (m, 1H), 5.09-5.01 (m, 1H), 3.86-3.52 (m, 5H), 2.36 (s, 3H).

Process 4: Production of 2-(4-bromo-2-methoxy-6-methylphenyl)cyclopent-4-ene-1,3-dione

To the mixed solution of 1.6 g of chromium oxide (trivalent) and 8.6 ml of water, 1.1 ml of concentrated sulfuric acid was added under cooling with ice. The reaction solution was added to a separately prepared mixed solution of 3.1 g of 5-(4-bromo-2-methoxy-6-methylphenyl)-4-hydroxycyclopent-2-enone and 28 ml of acetone under cooling with ice and the resultant reaction solution was stirred for 25 minutes. After completion of the reaction, 30 ml of isopropyl alcohol was added to the reaction solution and the solvent was distilled away under reduced pressure. To the obtained residue, 30 ml of ethyl acetate was added and the resultant mixture was dehydrated and dried with saturated sodium chloride aqueous solution and then anhydrous sodium sulfate in this order, followed by distilling away the solvent under reduced pressure. The obtained solid was washed with diisopropyl ether to give 1.8 g of the target compound as a yellow solid.

Melting point; 104° C. to 107° C.

Process 5: Production of 2-(4-bromo-2-methoxy-6-methylphenyl)-3-hydroxy-5-(2-oxopropyl)cyclopent-2-enone

To the mixed solution of 1.8 g of 2-(4-bromo-2-methoxy-6-methylphenyl)cyclopent-4-ene-1,3-dione and 30 ml of N,N-dimethylformamide, 1.7 g of potassium carbonate and 0.85 g of methyl acetoacetate were sequentially added, and the resultant reaction solution was stirred at room temperature for 15 hours. After completion of the reaction, 1 mol/L of a hydrochloric acid aqueous solution was added to the reaction solution to adjust the pH to 3 and the mixture was extracted with 30 ml of ethyl acetate. The obtained organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and then anhydrous sodium sulfate in this order and the solvent was distilled away under reduced pressure. To the obtained residue, 20 ml of methanol and 5 ml of water were added, and 1 g of potassium hydroxide was further added to the resultant mixture, followed by stirring the obtained mixture at room temperature for 15 hours. After completion of the reaction, the solvent was distilled away under reduced pressure. To the obtained residue, 20 ml of 1 mol/L of a hydrochloric acid aqueous solution was added and the resultant mixture was extracted with 20 ml of ethyl acetate. The obtained organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and then anhydrous sodium sulfate in this order and the solvent was distilled away under reduced pressure to give 1.8 g of the target compound as a brown viscous product.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.02 (brs, 1H), 6.88 (brs, 1H), 3.91-3.62 (m, 3H), 3.51-1.97 (m, 12H).

Synthesis Example 6: Production of 2-(4-bromo-2-methoxy-6-methylphenyl)-3-hydroxy-5-{2-(methoxyimino)propyl}cyclopent-2-enone (Compound No. 6-076)

This compound was produced from 2-(4-bromo-2-methoxy-6-methylphenyl)-3-hydroxy-5-(2-oxopropyl)cyclopent-2-enone by a similar method to the method in Synthesis Example 3.

Melting point; 150° C. to 153° C.

Synthesis Example 7: Production of 2-(4′-chloro-3-methoxy-5-methyl-[1,1′-biphenyl]-4-yl)-3-hydroxy-5-{2-(methoxyimino)propyl}cyclopent-2-enone (Compound No. 6-077)

To the mixed solution of 1.1 g of 2-(4-bromo-2-methoxy-6-methylphenyl)-3-hydroxy-5-{2-(methoxyimino)propyl}cyclopent-2-enone, 540 mg of 4-chlorophenylboronic acid, 8 ml of 1,4-dioxane, and 2.5 ml of water, 2.2 g of tripotassium phosphate and 237 mg of [1,1′-bis(diphenylphosphino)ferrocene] palladium (II) dichloride dichloromethane adducts were sequentially added. After completion of the addition, the reaction container was purged with nitrogen gas and thereafter the resultant mixture was stirred at 100° C. for 2 hours. After completion of the reaction, 1 mol/L of a hydrochloric acid aqueous solution was added to the reaction mixture to adjust the pH to 3 and the obtained mixture was extracted with 10 ml of ethyl acetate. The obtained organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and then anhydrous sodium sulfate in this order and thereafter the solvent was distilled away under reduced pressure. The obtained residue was purified with medium pressure preparative liquid chromatography eluting the residue with n-hexane-ethyl acetate (gradient from 8:1 to 1:1) to give 1.1 g of the target compound as an orange viscous product.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 11.36 (brs, 1H), 7.59-7.34 (m, 4H), 7.09-6.87 (m, 2H), 4.00-3.78 (m, 6H), 3.54-3.32 (m, 1H), 3.09-2.50 and 2.38-1.81 (m, 10H).

Synthesis Example 8: Production of 2-(4′-chloro-3-methoxy-5-methyl-[1,1′-biphenyl]-4-yl)-4-{2-(methoxyimino)propyl}-3-oxocyclopent-1-ene-1-yl morpholine-4-carboxylate (Compound No. 6-078)

To the mixed solution of 70 mg of 2-(4′-chloro-3-methoxy-5-methyl-[1, 1′-biphenyl]-4-yl)-3-hydroxy-5-{2-(methoxyimino)propyl}cyclopent-2-enone and 3 ml of N,N-dimethylformamide, 35 mg of potassium carbonate and then 31 mg of 4-morpholinylcarbonyl chloride were sequentially added, and the resultant reaction solution was stirred at room temperature for 3 hours. After completion of the reaction, 5 ml of water was added to the reaction solution and the resultant mixture was extracted with 5 ml of ethyl acetate. The obtained organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and then anhydrous sodium sulfate in this order and thereafter the solvent was distilled away under reduced pressure. The obtained residue was purified with medium pressure preparative liquid chromatography eluting the residue with n-hexane-ethyl acetate (gradient from 3:1 to 1:1) to give 77 mg of the target compound as a colorless oily product.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.58-7.34 (m, 4H), 7.03 (s, 1H), 6.90-6.86 (m, 1H), 3.92-3.22 (m, 15H), 3.09-2.68 (m, 3H), 2.40-2.13 (m, 4H), 1.88 (s, 3H).

Synthesis Example 9: Production of 3-hydroxy-2-(2-methoxy-4,6-dimethylphenyl)-5-{2-(methoxyimino)propyl}cyclopent-2-enone (Compound No. 6-037)

To the mixed solution of 1 g of 2-(4-bromo-2-methoxy-6-methylphenyl)-3-hydroxy-5-{2-(methoxyimino)propyl}cyclopent-2-enone, 326 mg of trimethylboroxine, and 25 ml of 1,4-dioxane, 1.1 g of potassium carbonate and 424 mg of [1,1′-bis(diphenylphosphino)ferrocene] palladium (II) dichloride dichloromethane adduct were sequentially added. After completion of the addition, the reaction container was purged with nitrogen gas and thereafter the resultant reaction mixture was stirred at 90° C. for 3 hours. After completion of the reaction, 1 mol/L of a hydrochloric acid aqueous solution was added to the reaction mixture to adjust the pH to 3 and the obtained mixture was extracted with 25 ml of ethyl acetate. The obtained organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and then anhydrous sodium sulfate in this order and thereafter the solvent was distilled away under reduced pressure. The obtained residue was purified with medium pressure preparative liquid chromatography eluting the residue with n-hexane-ethyl acetate (1:1) to give 496 mg of the target compound as an orange viscous product.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 11.00 (brs, 1H), 6.78-6.53 (m, 2H), 4.05-3.70 (m, 6H), 3.50-3.28 (m, 1H), 3.00-2.55 (m, 3H), 2.40-1.80 (m, 10 OH).

Synthesis Example 10: Production of mixture of 3-(benzyloxy)-2-mesityl-5-{2-(methoxyimino)propyl}cyclopent-2-enone and 3-(benzyloxy)-2-mesityl-4-{2-(methoxyimino)propyl}cyclopent-2-enone (Compound No. 1-009)

To the mixed solution of 500 mg of 3-hydroxy-2-mesityl-5-{2-(methoxyimino)propyl}cyclopent-2-enone and 6 ml of acetone, 458 mg of potassium carbonate and then 341 mg of benzyl bromide were sequentially added, and the resultant reaction solution was stirred at room temperature for 18 hours. After completion of the reaction, 20 ml of water was added to the reaction solution and the resultant mixture was extracted with 20 ml of ethyl acetate. The obtained organic phase was washed with water, dehydrated and dried with saturated sodium chloride aqueous solution and then anhydrous sodium sulfate in this order and thereafter the solvent was distilled away under reduced pressure. The obtained residue was purified with medium pressure preparative liquid chromatography eluting the residue with n-hexane-ethyl acetate (gradient from 5:1 to 1:1) to give 680 mg of the target compound as a colorless oily product.

¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.28-7.03 (m, 5H), 6.92-6.80 (m, 2H), 4.97-4.92 and 4.73-4.68 (m, 2H), 3.86-3.77 (m, 3H), 3.31-1.80 (m, 17H).

The obtained target compound was a mixture of 1-009a-1, 1-009a-2, 1-009b-1, and 1-009b-2 and the mixing ratio thereof was 16:3:8:1. The mixing ratio was determined by qualitative analysis with high performance liquid chromatography [mobile phase; {(acetonitrile:water=4:1)+acetic acid of a volume ratio of 1%}, measurement wavelength: 254 nm]. The structures of 1-009a-1, 1-009a-2, 1-009b-1 and 1-009b-2 are as follows.

Synthesis Example 11: Production of 3-(benzyloxy)-2-mesityl-5-{2-(methoxyimino)propyl}-5-methylcyclopent-2-enone (Compound No. 11-001) and 3-(benzyloxy)-2-mesityl-4-{2-(methoxyimino)propyl}-5-methylcyclopent-2-enone (Compound No. 12-001)

The mixed solution of the mixture of 611 mg of 3-(benzyloxy)-2-mesityl-5-{2-(methoxyimino)propyl}cyclopent-2-enone and 3-(benzyloxy)-2-mesityl-4-{2-(methoxyimino)propyl}cyclopent-2-enone (Compound No. 1-009) and 7 ml of tetrahydrofuran was cooled to −78° C. under a nitrogen atmosphere and thereafter 1.7 ml of lithium diisopropylamide (mixed solution of about 1.5 mol/L of n-hexane and tetrahydrofuran, manufactured by KANTO CHEMICAL CO., INC.) was added dropwise to the mixed solution. After completion of the dropwise addition, the reaction mixture was stirred at the same temperature for 30 minutes. After completion of the stirring, 244 mg of iodomethane was added to the reaction mixture. After completion of the addition, the reaction mixture was warmed to room temperature and stirred at the same temperature for 30 minutes. After completion of the reaction, the reaction mixture was added to 30 ml of ice water and the resultant mixture was extracted with 20 ml of ethyl acetate. The obtained organic phase was washed with water, dehydrated and dried with anhydrous sodium sulfate and thereafter the solvent was distilled away under reduced pressure. The obtained residue was purified by high performance liquid chromatography eluting the residue with acetonitrile-water [4:1 (volume ratio)] to give 173 mg of Compound No. 11-001 as a colorless oily product and 86 mg of Compound No. 12-001 as a colorless oily product.

Compound No. 11-001: ¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.39-7.12 (m, 5H), 6.86 (brs, 2H), 4.96 (s, 2H), 3.81 (s, 3H), 3.27-3.13 (m, 1H), 2.61-2.22 (m, 6H), 2.06 (brs, 6H), 1.87-1.77 (m, 3H), 1.26 (s, 3H).

Compound No. 12-001: ¹H NMR (CDCl₃, Me₄Si, 300 MHz) δ 7.37-7.25 (m, 3H), 7.14-7.04 (m, 2H), 6.86 (brs, 2H), 4.71 (s, 2H), 3.83 (s, 3H), 2.88-2.77 (m, 2H), 2.47-2.23 (m, 5H), 2.15-2.02 (m, 6H), 1.88 (s, 3H), 1.37-1.22 (m, 3H).

The synthesis examples of production intermediates for producing the compounds of the present invention will be specifically described as Reaction Example 1 and Reaction Example 2 below. The production intermediates of the present invention, however, are not limited to only these Reaction Examples.

Reaction Example 1: Production of 2-(2,6-dimethoxy-4-methylphenyl)cyclopent-4-ene-1,3-dione Process 1: Production of (2,6-dimethoxy-4-methylphenyl)(furan-2-yl)methanol

The mixed solution of 0.69 g of furan and 10 ml of tetrahydrofuran was cooled to −10° C. under a nitrogen atmosphere. To the mixed solution, 6.9 ml of n-butyllithium (1.6 M of a tetrahydrofuran solution) was added, and the resultant reaction solution was stirred at the same temperature for 1 hour and 30 minutes. The mixed solution of 2.0 g of 2,6-dimethoxy-4-methylbenzaldehyde and 10 ml of tetrahydrofuran was added at −10° C. to the reaction solution and then the temperature of the resultant reaction solution was raised to room temperature, followed by stirring the resultant reaction solution for 12 hours. After completion of the reaction, the reaction solution was poured to ice water and the resultant mixture was extracted with 20 ml of ethyl acetate. The obtained organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and then anhydrous sodium sulfate in this order and the solvent was distilled away under reduced pressure. The obtained residue was purified with medium pressure preparative liquid chromatography eluting the residue with n-hexane-ethyl acetate (3:1) to give 1.89 g of the target compound as a pale yellow solid.

Melting point; 75° C. to 85° C.

Process 2: Production of 2-(2,6-dimethoxy-4-methylphenyl)cyclopent-4-ene-1,3-dione

The mixed solution of 100 mg of (2,6-dimethoxy-4-methylphenyl)(furan-2-yl)methanol and 1 ml of water was irradiated with microwaves (200 W) using the microwave synthesizing apparatus and the resultant reaction solution was stirred at 200° C. for 30 minutes. After completion of the reaction, the reaction solution was extracted with 3 ml of ethyl acetate. The obtained organic phase was dried with anhydrous sodium sulfate and the solvent was distilled away under reduced pressure. To the obtained residue, 5 ml of dichloromethane and 0.13 g of pyridinium chlorochromate were sequentially added and, after completion of the addition, the resultant reaction solution was stirred at room temperature for 2 hours. After completion of the reaction, 5 ml of isopropyl alcohol was added to the reaction solution and the solvent was distilled away under reduced pressure. To the obtained residue, 10 ml of water was added and the resultant mixture was extracted with 10 ml of ethyl acetate. The obtained organic phase was dehydrated and dried with saturated sodium chloride aqueous solution and then anhydrous sodium sulfate in this order and the solvent was distilled away under reduced pressure. The obtained residue was purified with medium pressure preparative liquid chromatography eluting the residue with n-hexane-ethyl acetate (2:1) to give 20 mg of the target compound as a yellow solid.

Melting point: 122° C. to 126° C.

Reaction Example 2: Production of 2-(2-methoxy-4,6-dimethylphenyl)cyclopent-4-ene-1,3-dione

As a yellow solid 0.2 g of 2-(2-methoxy-4,6-dimethylphenyl)cyclopent-4-ene-1,3-dione was obtained by the similar method to Process 1 to Process 4 of Synthesis Example 5 using 10.0 g of 2-methoxy-4,6-dimethylaniline synthesized by the method described in J. Am. Chem. Soc. 2000, Vol. 122, P. 5043 as a raw material.

Melting point; 123° C. to 125° C.

The compound of the present invention can be synthesized in accordance with the above production examples. Examples of the compounds of the present invention produced in a similar manner to Synthesis Examples 1 to 11 are listed in Table 5 to Table 20. The present invention, however, is not limited to these examples. In Tables, the expression of Me is methyl group. Similarly, the expression of Et is ethyl group, n-Pr and Pr-n are normal-propyl group, i-Pr and Pr-i are iso-propyl group, c-Pr and Pr-c are cyclopropyl group, n-Bu and Bu-n are normal-butyl group, s-Bu and Bu-s are secondary-butyl group, i-Bu and Bu-i are iso-butyl group, t-Bu and Bu-t are tertiary-butyl group, c-Bu and Bu-c are cyclobutyl group, n-Pen and Pen-n are normal-pentyl group, c-Pen and Pen-c are cyclopentyl group, n-Hex and Hex-n are normal-hexyl group, c-Hex and Hex-c are cyclohexyl group, Hept is heptyl group, Oct is octyl group, and Ph is phenyl group. The structures of D1-1a, D1-2c, D1-5d, D1-5e, D1-6d, D1-7a, D1-7b, D1-8b, D1-10d, D1-11a, D1-22a, D1-32a, D1-32b, D1-33b, D1-34a, D1-37a, D1-81a, D1-84a, D1-103a, D1-103b, D1-103c, D1-103d, D1-103e, D1-103f, D1-103g, D1-103h, D1-103i, D1-103j, D1-103k, D1-103l, D1-103m, D1-103n, D1-108b, D1-108c, D1-108d, and D1-108e are the following structures. The numbers shown in the structural formulas of D1-5d, D1-5e, D1-6d, D1-7b, D1-10d, D1-32b, and D1-33b are the substitution positions of X¹. The numbers shown in the structural formula of D1-108b are the substitution positions of Z³. The numbers shown in the structural formula of D1-108c are the substitution positions of Z¹. The numbers shown in the structural formula of D1-108d are the substitution positions of Z².

In Tables, the expression of “m. p.” means a “melting point”, the expression of “*1” means “resinous”, and the expression of “decomp.” means decomposition.

TABLE 5

No. R6 R7 A m.p. (° C.) 1-001 Me Me Me 92-98 1-002 Me Me H 170-173 1-003 Me Et H 135-140 1-004 Me Me C(O)Bu-t *1 1-005 Me Me C(O)Me *1 1-006 Me Me S(O)₂Me *1 1-007 Me Me CH₂CH═CH₂ *1 1-008 Me Me CH₂C≡CH *1 1-009 Me Me CH₂Ph *1 1-010 Me Me C(O)Ph *1 1-011 Me Me CH₂CH₂SMe *1 1-012 Me Me CH₂C(O)OMe *1 1-013 Me Me CH₂CN *1 1-014 Me Me C(O)OMe *1 1-015 Me Me C(O)Pr-c *1 1-016 Me Me C(O)C(Me)₂CH₂Cl *1 1-017 Me Me C(O)C(Me)₂OPh *1 1-018 Me CH₂CH═CH₂ H 119-120 1-019 Me CH₂C≡CH H 113-114 1-020 Me CH₂Ph H 190-192 1-022 Me CH₂(D1-32a) H 118-120 1-023 Me CH₂C(O)OMe H 100-102 1-024 Me CH₂Pr-c H 138-140 1-025 Me CH₂C(O)(D1-103a) H 152-156 1-026 Me CH₂{D1-108c(2-F)} H 198-200 1-027 Me CH₂CH(OH)Me H 143-144 1-028 Me CH₂CF₃ H 172-174 1-029 Me CH₂CH₂SMe H  94-102 1-031 Me Me CH₂C≡CSi(Me)₃ *1 1-033 Me Me C(O)Oct-n *1 1-034 Me Me C(O)C(Me)₂OC(O)Me *1 1-035 Me Me C(O)CH₂CH₂Hex-C *1 1-036 Me Me C(O)(D1-103b) *1 1-037 Me Me CH₂CH₂OMe *1 1-038 Et Me H 147-149 1-039 Me Me C(O)C(Me)₂F *1 1-040 CH₂OMe Me H 150-153 1-041 Me CH₂CH₂OMe H 129-132 1-042 Me Me C(O)CH(Me)Cl *1 1-043 Me Me C(O)CH₂OPh *1 1-044 Me Me C(O)CH₂O{D1-108d(4-Cl)} *1 1-045 D1-32a Me H *1 1-046 c-Pr Me H *1 1-047 Ph Me H *1 1-048 i-Pr Me H *1 1-050 H Me H  96-108 1-051 Me Me C(O)C(Me)₂O{D1-108d(4-Cl)} *1 1-052 Me i-Pr H  93-95 1-053 Me t-Bu H 145-147 1-054 Me n-Hept H 136-137 1-055 Me CH₂CH₂Si(Me)3 H 133-135 1-056 Me CH₂CH═CHCl H 100-102 1-057 Me Ph H 149-151 1-058 Me H H 95-98 1-059 t-Bu Me H 163-164 1-060 Me Me C(O)CH(Me)OPh *1 1-062 n-Pr Me H 134-137 1-063 c-Pr Me C(O)CH₂OPh *1 1-064 Me Me C(O)C(Me)₂O{D1-108d(2-Cl)} *1 1-065 Me Me C(O)C(Me)₂O{D1-108d(3-Cl)} *1 1-066 s-Bu Me H 154-156 1-067 Me Me C(O)CH₂O{D1-108d(2-OMe)} *1 1-068 Me Me C(O)CH₂O{D1-108d(3-OMe)} *1 1-069 Me Me C(O)CH₂O{D1-108d(4-OMe)} *1 1-070 CH₂Pr-c Me H 153-155 1-071 Me Me C(O)CH₂O{D1-108d(2-NO₂)} *1 1-072 Me Me C(O)CH₂O{D1-108d(4-Me)} *1 1-073 Me Me C(O)CH₂O{D1-108d(4-F)} *1 1-074 Me Me C(O)CH₂O{D1-108d(3-CN)} *1 1-075 Me Me C(O)CH₂O{D1-108d[2,4-(Cl)₂]} *1 1-076 Me Me C(O)(D1-81a) *1 1-077 CH₂Cl Me Me *1 1-078 c-Pen Me H 161-163 1-079 Me Me C(O)CH₂O{D1-108d(4-CHO)} *1 1-080 Me Me C(O)CH₂O{D1-108d[4-C(O)OMe]} *1 1-081 Me Me C(O)CH₂O{D1-108d(4-Br)} *1 1-082 Me Me C(O)CH₂O{D1-108d(4-I)} *1 1-083 Me Me C(O)CH₂O(DH1-108e) *1 1-084 CH₂Cl Me H 159-161 1-085 c-Hex Me H 149-152 1-086 CH═CH₂ Me H 115-117 1-087 Me Me C(O)CH(Me)O(D1-103d) *1 1-088 Me Me C(O)(D1-103e) *1 1-089 Me Me C(O)(D1-103f) *1 1-090 Me Me C(O)CH═CHPr-n *1 1-091 Me Me C(O)CH═CH(D1-1a) *1 1-092 Me Me C(O)CH₂OCH₂CF₃ *1 1-093 Me Me C(O)CH₂OMe *1 1-094 Me Me C(O)CH₂OCH₂Ph *1 1-095 Me Me C(O)C≡CMe *1 1-096 Me Me C(O)C≡CSi(Me)₃ *1 1-097 CF₃ Me H 115-118 1-098 Me Me C(O)C(═NOMe)CH₂SMe *1 1-099 Me Me C(O){D1-6d(4,5-Cl₂)} *1 1-100 Me Me C(O){D1-5d(5-Me)} *1 1-101 Me Me C(O){D1-10d(2,5-Me₂)} *1 1-102 Me CH₂CN H 163-166 1-103 Me Me C(O){D1-5e(5-Pr-c)} *1 1-104 Me Me C(O)(D1-103a) *1 1-105 Me CH₂C(═NOMe)Me H 118-122 1-106 Me c-Pen H 120-122 1-107 Me Me S(O)₂C₈H₁₇ *1 1-108 Me Me C(O)N(Me)₂ *1 1-109 Me CH₂(D1-103g) H 155-158 1-110 Me CH₂CH₂S(O)₂Me H 130-132 1-111 Me CH₂(D1-84a) H 150-153 1-112 Me C(O)CH₂O{D1-108c(4-OMe)} H 179-180 1-113 Me C(O)CH₂O{D1-108c(2-Cl)} H 194-197 1-114 Me C(O)CH₂O{D1-108c(3-Cl)} H 188-193 1-115 Me C(O)CH₂O{D1-108c(2-Cl,6-F)} H 225-228 1-116 Me C(O)CH₂O{D1-108c(2-CF₃)} H 147-154 1-117 Me C(O)CH₂O{D1-108c(3-CF₃)} H 143-154 1-118 Me C(O)CH₂O{D1-108c[4-C(O)OMe]} H 183-189 1-119 Me C(O)CH₂O{D1-108c(2-NO₂)} H 177-179 1-120 Me D1-103h H 162-166 1-121 Me CH₂CH(Cl)Me H 182-185 1-122 Me Me SO₂N(Me)₂ *1 1-123 Me n-Pr H 123-126 1-124 Me CH₂C(O)NH₂ H 120-123 1-125 Me CH₂CH₂S(O)Me H *1 1-126 Me Me C(O)N(Me)(CH2)4Cl *1 1-127 Me Me C(O)N(i-Pr)Ph *1 1-128 Me Me C(O)N(i-Pr){D1-108d(4-F)} *1 1-129 Me Me C(O)N(i-Pr){D1-108d(2,4-F₂)} *1 1-130 Me Me C(O)N(Et)CH₂C(Me)═CH₂ *1 1-131 c-Pr CH₂CF₃ H 137-138 1-132 Me CH₂CH₂NH₂ H 209 (decomp.) 1-133 D1-108c(4-F) Me H 181-183 1-134 Me Me C(O)CH₂SPh *1 1-135 Me CH₂CH(Br)Me H 179-181 1-136 Me C(O){D1-108c(4-F)} H 171-180 1-137 Me C(O){D1-108c(4-Cl)} H 135-150 1-138 Me C(O){D1-108c(4-CF₃)} H 168-173 1-139 Me Me C(O)CH₂N(Me)C(O)Ph *1 1-140 Me Me C(O)CH(Et)O(D1-103i) *1 1-141 Me Me C(S)N(Me)₂ *1 1-142 Me Me SO₂(CH₂)₃Cl *1 1-143 Me Me SO₂Pr-c *1 1-144 Me Me SO₂(CH₂)₂Si(Me)₃ *1 1-145 Me Me C(O)OCH₂Ph *1 1-146 Me Me C(O)OCH₂CH═CH₂ *1 1-147 Me Me C(O)O(CH₂)₂OMe *1 1-148 Me Me C(O)C(Me)₂{D1-108d(4-Cl)} *1 1-149 Me Me C(O){D1-108d(4-CF₃)} *1 1-150 Me Me C(O)(D1-103j) *1 1-151 Me Me C(O)(D1-103k) *1 1-152 Me Me C(O)(D1-103l) *1 1-153 Me Me C(O)N(CH₂CH═CH₂)₂ *1 1-154 Me Me C(O){D1-108d(2-CF₃)} 90-92 1-155 Me Me C(O){D1-108d(2-OCF₃)} *1 1-156 Me Me C(O)CH₂{D1-108d(4-OMe)} *1 1-157 Me Me C(O)N(Ph)₂ 165-168 1-158 Me Me C(O)N(i-Pr)₂ 74-75 1-159 Me Me C(O)N(Me)Ph *1 1-160 Me Me C(O)(D1-8b) *1 1-161 Me Me SO₂{D1-108d(4-Me)} *1 1-162 Me Me C(O){D1-108d[2-Cl, 3-C(O)OMe, 4-SO₂Me]} *1 1-163 Me Me C(O)CH9Me)O(D1-103m) *1 1-164 D1-108c(4-Me) Me H *1 1-165 Me Me c-Pen *1 1-166 Me Me CH₂C(Cl)═CHCl *1

Compound No. 1-009 of the present invention is the mixture of Compound Nos. 1-009a-1, 1-009a-2, 1-009b-1, and 1-009b-2 in Synthesis Example 10 described above. Compound Nos. 1-009a-1 and 1-009a-2 and Compound Nos. 1-009b-1 and 1-009b-2 are respective geometric isomers of the oxime moiety.

TABLE 6

No. R⁶ R⁷ R^(8a) R^(9a) A m.p. (° C.) 1-021 Me Me C(═NOMe)Me H H 163-164 1-030 H Me Me Me H 176-180 1-032 Me Me Me H H 199-206 1-049 Me Me D1-108c(4-F) H H 160-168 1-061 Me Me CF₃ H H 155-158

TABLE 7

No. R⁶ R^(8a) R^(9a) A m.p. (° C.) 2-001 Me H H H 183-185 2-002 Me C(O)Me H H 190-193 2-003 Me C(O)OMe H H 155-158 2-004 Me C(O)OEt Me H 154-163 2-005 Me Me H H 153-158 2-006 Et H H H 197-198 2-007 CH₂OMe H H H 143-145 2-008 Ph C(O)OEt H H *1 2-009 i-Pr C(O)OEt H H 150-153 2-010 CF₃ C(O)OEt H H *1 2-011 CH₂Ph C(O)OEt H H 110-114 2-012 Me C(O)OEt Et H 140-144 2-013 D1-32a C(O)OEt H H 79-88 2-014 c-Pr C(O)OMe H H 204-206 2-015 CH₂Ph H H H *1 2-016 i-Pr H H H 139-144 2-017 c-Pr H H H 191-192 2-018 Me H H C(O)Bu-t *1 2-019 t-Bu C(O)OMe H H 192-194 2-020 n-Pr C(O)OMe H H 164-167 2-021 n-Pr H H H 190-193 2-022 t-Bu H H H 50-54 2-023 Me C(O)OMe Et H 160-163 2-024 s-Bu H H H 112-115 2-025 CH₂Pr-c C(O)OEt H H 132-134 2-026 CH₂Pr-c H H H 195-197 2-027 c-Pen O(O)OEt H H 168-170 2-028 c-Pen H H H 147-149 2-029 c-Hex C(O)OEt H H 154-157 2-030 c-Hex H H H 167-169 2-031 CH═CH₂ H H H 123-126 2-032 D1-108c(4-F) H H H 194-196

TABLE 8

No. R⁶ R⁷ A m.p. (° C.) 3-001 H Me H *1 3-002 Me Me H *1

TABLE 9

No. R⁶ R⁷ R^(8a) R^(8b) R^(9a) R^(9b) A m.p. (° C.) 4-001 Et Me H H H H H *1

TABLE 10

No. R⁶ R^(8a) R^(8b) R^(9a) R^(9b) A m.p. (° C.) 5-001 Et H H H H H *1 5-002 Et H H H H Me *1

TABLE 11

No. Z^(a) Z^(c) Z^(e) R^(8a) A m.p. (° C.) 6-001 Et Br Me H H 151-153 6-002 Et Br Me C(O)OMe H 184-188 6-003 Me Br Me H H 164-166 6-004 Me D1-7b(X¹═4-Cl) Me H H *1 5-005 Et D1-7b(X¹═4-Cl) Me H H *1 6-006 Et C≡CMe Me H H *1 6-007 Et Me Me H H 122-125 6-008 Et C≡CSi(Me)₃ Me H H *1 6-009 Me C≡CMe Me H H 60-65 6-010 Me C≡CPr-c Me H H *1 6-011 Me Br Me H Me *1 6-012 Me Ph Me H Me *1 6-013 Me D1-108b(4-Me) Me H Me *1 6-014 Me D1-108b(4-CF₃) Me H Me *1 6-015 Me Ph Me H H 167-169 6-016 Me D1-108b(4-CF₃) Me H H 163-164 6-017 Me D1-108b(4-OMe) Me H H 155-157 6-018 Me D1-108b(4-Me) Me H H 137-139 6-019 Me D1-108b(4-Cl) Me H Me *1 6-020 Me D1-108b(4-OMe) Me H Me 124-125 6-021 Me D1-108b(4-SMe) Me H Me 65-66 6-022 Me S(D1-103c) Me H H *1 6-023 Me C(O)OMe Me H H *1 6-024 Me SMe Me H H *1 6-025 Me C≡CCH₂OH Me H H *1 6-026 Me C(O)Me Me H H *1 6-027 Me CN Me H H 181-164 6-028 Me D1-32a Me H Me 151-154 6-029 Me D1-108b(4-Cl) Me H H 145-150 6-030 Me D1-108b(4-SMe) Me H H 167-169 6-031 Me CH═CH₂ Me H H 166-172 6-032 Me NO₂ Me H H 181-183 6-033 Me NHC(O)OBu-t Me H H *1 6-034 Me D1-108b(3-Cl) Me H H 197-199 6-035 Me D1-33b(6-Cl) Me H H *1 6-036 Me C≡CC(Me)₂OH Me H H *1 6-037 OMe Me Me H H *1 6-038 Br Me Me H H *1 6-039 Me c-Pr Me H Me *1 6-040 Me D1-7a Me H Me 129-132 6-041 Me OPh Me H Me *1 6-042 Me OCH₂CF₃ Me H Me 117-119 6-043 Me D1-108b(4-OCF₃) Me H Me *1 6-044 Me D1-37a Me H Me 166-169 6-045 Me OCH₂Ph Me H Me *1 6-046 Me OCH₂(D1-34a) Me H Me *1 6-047 Me O{D1-32b(5-CF₃)} Me H Me *1 6-048 Me OMe Me H Me 82-85 6-049 Me OCH₂CF₃ Me H H 165-172 6-050 Me c-Pr Me H H 170-178 6-051 Me D1-32a Me H H *1 6-052 Me OPh Me H H *1 6-053 Me OCH₂(D1-34a) Me H H 118-122 6-054 Me O{D1-32b(5-CF₃)} Me H H 169-172 6-055 Me OMe Me H H 141-143 6-056 Me D1-108b(4-OCF₃) Me H H 161-163 6-057 Me D1-37a Me H H 183-188 6-058 Me D1-108b(4-F) Me H H 159-161 6-059 Me D1-108b(4-F) Me H C(O)(D1-103a) *1 6-060 Me D1-108b(4-F) Me H S(O)₂N(Me)₂ *1 6-061 Me D1-108b(4-Cl) Me H C(O)CH₂OPh *1 6-062 Me D1-108b(4-Cl) Me H C(O)(D1-103a) *1 6-063 Me D1-108b(4-Cl) Me H C(O)N(Me)₂ *1 6-064 Et D1-108b(4-Cl) Me H C(O)(D1-103a) *1 6-065 Me C(═NOMe)Me Me H H 177-180 6-066 Et D1-108b(4-Cl) Me H H 165-167 6-067 Me CH═CHPr-n Me H Me *1 6-068 Me CH═CHPh Me H Me 125-126 6-069 Me OH Me H Me 192-195 6-070 Me OCH₂(D1-34a) Me H H *1 6-071 Me CH═CHPr-n Me H H 171-177 6-072 Me CH═CHPh Me H H 150-152 6-073 Me D1-7a Me H H 200-203 6-074 Me D1-22a Me H H 164-167 6-075 SMe Me Me H H *1 6-076 OMe Br Me H H 150-153 6-077 OMe D1-108b(4-Cl) Me H H *1 6-078 OMe D1-108b(4-Cl) Me H C(O)(D1-103a) *1 6-079 OMe D1-108b(4-Cl) Me H C(O)CH₂OPh *1 6-080 Me D1-108b(4-Cl) Me H C(O)CH₂CH₂CH₂C(O)Me *1 6-081 OMe D1-108b(4-Cl) Me H C(O)N(Me)₂ *1 6-082 Me D1-108b(4-Cl) Me H C(O)SBu-t *1 6-083 Me D1-108b(4-Cl) Me H CH₂OC(O)Ph *1 6-084 Me D1-108b(2-F,4-Cl) Me H H 175-177 6-085 Me D1-108b(3-Cl,4-F) Me H H 187-190 6-086 Me D1-108b(4-Cl) Me H C(O)CH(Me)CH₂SMe *1 6-087 Me D1-108b(3,5-Cl₂) Me H H 205-215 6-088 Me D1-108b(2,4-Cl₂) Me H H 148-151 6-089 Me D1-108b(2-F,4-Cl) Me H C(O)(D1-103a) *1 6-090 Me D1-108b(2,4-Cl₂) Me H C(O)(D1-103a) *1 6-091 OMe Me Me H C(O)CH₂OPh *1 6-092 Me D1-108b(2,4-Cl₂) Me H C(O)CH₂OPh *1 6-093 Me D1-108b(3-Cl,4-F) Me H C(O)(D1-103a) *1 6-094 OMe Me Me H C(O)(D1-103a) *1 6-095 OMe Me Me H S(O)₂N(Me)₂ *1 6-096 OMe Br F H H 157-159 6-097 Me OCH₂CH₂OME Me H Me *1 6-098 Me OCH₂CH₂OMe Me H H 119-121 6-099 OMe Ph Me H H 175-177 6-100 OMe Ph Me H C(O)CH₂OPh *1 6-101 Me D1-11a Me H Me *1 6-102 Me D1-22a Me H Me 103-104 6-103 OMe Me OMe H H 171-175 6-104 Me D1-108b(3,4,5-F₃) Me H H 161-163 6-105 Me D1-34a Me H H *1 6-106 Me D1-2c Me H H 204-207 6-107 OMe Ph F H H 175-177 6-108 OMe Me F H H *1 6-109 OMe Me Me H C(O)N(Me)₂ *1 6-110 OMe Me Me H C(O)(D1-103j) *1 6-111 OMe Me Me H C(O)(D1-103k) *1 6-112 Me H Me H H 167-170 6-113 OMe Br Me Me H *1 6-114 OMe Me Me Me H *1 6-115 OMe Me Me H C(O)N(Et)₂ *1 6-116 OMe Me Me H C(S)N(Et)₂ *1 6-117 OMe Me Me H C(O)Bu-t *1 6-118 OMe Me Me H C(O){D1-108d[4-C(O)N(Me)₂]} *1 6-119 OMe Me Me H C(S)OPh *1 6-120 OMe Me Me H C(O)CH═CH₂ *1 6-121 OMe Me Me H C(O)Ph *1 6-122 OMe Me Me H C(O)CH₂OC(O)Me *1 6-123 OMe Me Me Me C(O)Bu-t *1 6-124 OMe Me Me H C(O)SBu-t *1 6-125 OMe Me Me H C(S)N(Me)₂ *1 6-126 OMe Me Me H C(O)CH₂CH₂CH₂Cl *1 6-127 OMe Me Me Me C(O)(D1-103a) *1

TABLE 12

No. Z^(a) Z^(c) Z^(e) R^(8a) A m.p. (° C.) 7-001 Et Br Me C(O)OMe H *1 7-002 Me Br Me H H 203-204 7-003 Et Br Me H H 170-172 7-004 Me Ph Me H H 196-200 7-005 Me D1-108b(4-CF₃) Me H H 174-176 7-006 Me D1-108b(4-OMe) Me H H 170-171 7-007 Me D1-108b(4-Me) Me H H 90-93 7-008 Me D1-108b(4-Cl) Me H H 173-175 7-009 Me D1-108b(4-SMe) Me H H 179-184 7-010 Me C≡CMe Me H H 207-209 7-011 Br Me Me H H 182-186 7-012 Me D1-32a Me H H 118-122 7-013 Me c-Pr Me H H 176-183 7-014 Me OPh Me H H 142-148 7-015 Me OCH₂CF₃ Me H H 122-125 7-016 Me D1-108b(4-OCF₃) Me H H 169-172 7-017 Me D1-37a Me H H *1 7-018 Me OCH₂Ph Me H H 156-158 7-019 Me O{D1-32b(5-CF₃)} Me H H 100-102 7-020 Me OMe Me H H 204-207 7-021 Me OCH₂(D1-34a) Me H H 187 (decomp.) 7-022 Me CH═CHPr-n Me H H 106-116 7-023 Me CH═CHPh Me H H 181-185 7-024 Me D1-7a Me H H 184-187 7-025 Me D1-11a Me H H 61-65 7-026 Me D1-22a Me H H 54-66 7-027 OMe Br Me H H *1 7-028 OMe Br F C(O)OMe H 210-213 7-029 OMe Br F H H 163-165 7-030 OMe Me Me H H 147-152 7-031 OMe Br Me Me H 93-95

TABLE 13

No. Q R⁶ A m.p. (° C.) 8-001 O Me H 178-182 8-002 O C(═NOMe)Me H 50-55 8-003 NOMe C(═NOMe)Me H 190 (decomp.)

TABLE 14

No. R⁶ R⁷ Z^(c) A m.p. (° C.) 9-001 i-Pr Me Br H 93-96 9-002 c-Pr Me Br H 167-168 9-003 i-Pr Me C≡CMe C(O)CH₂OPh *1 9-004 i-Pr Me D1-7b(X¹═4-Cl) H *1 9-005 i-Pr Me C≡CSi(Me)₃ H *1 9-006 i-Pr Me C≡CMe H 176-173 9-007 c-Pr Me D1-7b(X¹═4-Cl) H *1 9-008 c-Pr Me C≡CMe H 170-173 9-009 c-Pr CH₂CF₃ Br H 128-130 9-010 Me CH₂CF₃ D1-7b(X¹═4-Cl) H 161-184 9-011 Me CH₂CF₃ C≡CMe H 158-161 9-012 Me CH₂CF₃ D1-7b(X¹═4-Cl) C(O)CH₂OPh *1 9-013 Me CH₂CF₃ C≡CMe C(O)CH₂OPh *1 9-014 i-Pr CH₂CF₃ D1-7b(X¹═4-Cl) H *1 9-015 i-Pr CH₂CF₃ C≡CMe H 189-192 9-016 Me CH₂CH₂OMe D1-7b(X¹═4-Cl) H 119-122 9-017 Me CH₂CH₂OMe Br H 70-74 9-018 i-Pr CH₂CH₂OMe Br H *1 9-019 c-Pr CH₂CH₂OMe Br H *1 9-020 c-Pr CH₂CH₂OMe D1-7b(X¹═4-Cl) H *1 9-021 c-Pr CH₂CH₂OMe C≡CMe H *1 9-022 i-Pr CH₂CH₂OMe D1-7b(X¹═4-Cl) H *1 9-023 i-Pr CH₂CH₂OMe C≡CMe H *1 9-024 Me CH₂CF₃ D1-108b(4-Cl) H 202-204 9-025 Me CH₂CF₃ D1-108b(4-Cl) C(O)(D1-103a) *1 9-026 Me CH₂CF₃ D1-108b(4-Cl) C(O)N(Me)₂ *1 9-027 Me CH₂CF₃ D1-108b(4-Cl) C(O)CH₂OPh *1 9-028 c-Pr Me Ph H 202-209 9-029 Me CH₂C(O)N(Me)₂ Br H *1 9-030 Me D1-103n Br H *1

TABLE 15

No. R⁶ R^(8a) Z^(c) A m.p. (° C.) 10-001 i-Pr C(O)OEt Br H 143-145 10-002 c-Pr C(O)OMe Br H 171-173 10-003 i-Pr H Br H 151-153 10-004 c-Pr H Br H 171-174

TABLE 16

No. R⁶ R⁷ R¹⁰ A m.p. (° C.) 11-001 Me Me Me CH₂Ph *1 11-002 Me Me Me H 165-168

TABLE 17

No. R⁶ R⁷ R¹¹ A m.p. (° C.) 12-001 Me Me Me CH₂Ph *1 12-002 Me Me Me H *1

TABLE 18

No. Z^(a) Z^(c) Z^(e) R⁶ A m.p. (° C.) 13-001 OMe Br Me Et H *1 13-002 OMe Me Me c-Pr H 81-84 13-003 OMe Me Me Et H 81-84 13-004 OMe Ph Me Et H 178-181 13-005 OMe Me Me c-Pr C(O)(D1-103a) *1 13-006 OMe Me Me c-Pr C(O)Bu-t *1

TABLE 19

No. Z^(a) Z^(c) Z^(e) R⁶ A m.p. (° C.) 14-001 OMe Br Me c-Pr H *1 14-002 OMe Br Me Et H *1

TABLE 20

No. Z^(a) Z^(c) Z^(e) R⁷ A m.p. (° C.) 15-001 OMe Me Me CH₂C≡CH H *1 15-002 OMe Me Me CH₂CH═CH₂ H *1 15-003 OMe Me Me CH₂Pr-c H *1 15-004 OMe Me Me CH₂CH₂OMe H *1 15-005 OMe Me Me CH₂CF₃ H *1 15-006 OMe Me Me CH₂CN H *1 15-007 OMe Me Me CH₂CH₂OMe C(O)(D1-103a) *1 15-008 OMe Me Me CH₂CH₂OMe C(S)N(Me)₂ *1 15-009 OMe Me Me CH₂CF₃ C(O)Bu-t *1 15-010 OMe Me Me CH₂CF₃ C(O)N(Me)₂ *1 15-011 OMe Me Me CH₂CN S(O)₂Me *1 15-012 OMe Me Me CH₂CN C(O)N(Et)₂ *1 15-013 OMe Me Me CH₂C≡CH C(O)OMe *1 15-014 OMe Me Me CH₂Pr-c C(O)SBu-t *1 15-015 OMe Me Me CH₂CH═CH₂ C(O)CH₂OPh *1 15-016 OMe Me Me CH₂C≡CH C(O)(D1-103j) *1 15-017 OMe Me Me CH₂CH═CH₂ C(O)(D1-103l) *1 15-018 OMe Me Me CH₂Pr-c C(O)(D1-103k) *1

In the compounds of the present invention, ¹H-NMR data of the compounds having no description of the melting point are listed in Table 21.

The chemical shift value of proton nuclear magnetic resonance was measured at 300 MHz in a deuterochloroform solvent using Me₄Si (tetramethylsilane) as a reference material. The symbols in Table 21 are the following meanings. s: singlet, brs: broad singlet, d: doublet, t: triplet, and m: multiplet. For the signals that can be analyzed when two or more structural isomers are present, the chemical shift values of each of the signals are marked with “and”.

TABLE 21 No. ¹H-NMR (CDCl₃, Me₄Si, 300 MHz) 1-004; 6.85-6.81(m, 2H), 3.87-3.82(m, 3H), 3.70-2.18(m, 8H), 2.15- 1.78(m, 9H), 1.08 and 1.06(s, 9H) 1-005; 6.90-6.85(m, 2H), 3.87-3.82(m, 3H), 3.77-2.18(m, 8H), 2.17- 1.98(m, 9H), 1.97-1.83(m, 3H) 1-006; 6.92-6.87(m, 2H), 3.84(s, 3H), 3.37-2.60(m, 7H), 2.40-2.24 (m, 4H), 2.13-2.02(m, 6H), 1.97-1.83(m, 3H) 1-007; 6.90-6.85(m, 2H), 5.90-5.67(m, 1H), 5.28-5.07(m, 2H), 4.50- 4.40 and 4.23-4.15(m, 2H), 3.88-3.78(m, 3H), 3.00-1.85 (m, 17H) 1-008; 6.90-6.80(m, 2H), 4.60-4.48 and 4.38-4.30(m, 2H), 3.90-3.75 (m, 3H), 3.31-2.35(m, 6H), 2.33-2.00(m, 9H), 1.97-1.85(m, 3H) 1-009; 7.28-7.03(m, 5H), 6.92-6.80(m, 2H), 4.97-4.92 and 4.73-4.68 (m, 2H), 3.86-3.77(m, 3H), 3.31-1.80(m, 17H) 1-009a-1: 7.35-7.30(m, 3H), 7.20-7.15(m, 2H), 6.90-6.85(m, 2H), 4.95 (s, 2H), 3.84(s, 3H), 3.00-2.80(m, 3H), 2.65-2.55(m, 1H), 2.27 (s, 3H), 2.25-2.15(m, 1H), 2.10-2.00(m, 6H), 1.86(s, 3H) 1-009a-2; 7.35-7.30(m, 3H), 7.20-7.15(m, 2H), 6.90-6.85(m, 2H), 4.95 (s, 2H), 3.80(s, 3H), 2.95-2.80(m, 2H), 2.76-2.70(m, 1H), 2.66- 2.57(m, 2H), 2.27(s, 3H), 2.10-2.00(m, 6H), 1.91(s, 3H) 1-009b-1; 7.31-7.28(m, 3H), 7.10-7.07(m, 2H), 6.87-6.85(m, 2H), 4.72 (s, 2H), 3.84(s, 3H), 3.30-3.20(m, 1H), 2.90-2.80(m, 1H), 2.80- 2.70(m, 1H), 2.42-2.37(m, 1H), 2.30-2.23(m, 4H), 2.08-2.05 (m, 6H), 1.86(s, 3H) 1-009b-2; 7.32-7.28(m, 3H), 7.10-7.07(m, 2H), 6.88-6.86(m, 2H), 4.74 (s, 2H), 3.83(s, 3H), 3.29-3.24(m, 1H), 2.82-2.63(m, 3H), 2.39- 2.34(m, 1H), 2.28(s, 3H), 2.10(s, 3H), 2.05(s, 3H), 1.92(s, 3 H) 1-010; 7.96-7.15(m, 5H), 6.90-6.87(m, 2H), 3.88-3.75(m, 3H), 3.55- 1.83(m, 17H) 1-011; 6.98-6.75(m, 2H), 4.20-4.77(m, 5H), 3.28-2.60(m, 6H), 2.45- 1.80(m, 16H) 1-012; 6.92-6.80(m, 2H), 4.69 and 4.53 and 4.35and 4.25(s, 2H), 3.88- 3.58(m, 6H), 3.38-3.28 and 3.00-1.80(m, 17H) 1-013; 6.98-6.87(m, 2H), 4.56 and 4.55 and 4.46 and 4.44(s, 2H), 3.92-3.82(m, 3H), 3.36-3.25 and 3.10-2.60(m, 4H), 2.60-1.80 (m, 13H) 1-014; 6.91-6.85(m, 2H), 3.85(s, 3H), 3.77 and 3.70(s, 3H), 3.35-3.18 (m, 1H), 3.10-2.65(m, 3H), 2.35-2.22(m, 4H), 2.10-2.02(m, 6H), 1.90-1.83(m, 3H) 1-015; 6.91-6.82(m, 2H), 3.90-3.80(m, 3H), 3.31-3.20(m, 1H), 3.07- 2.78(m, 3H), 2.35-2.20(m, 4H), 2.10-2.00(m, 6H), 1.95-1.83 (m, 3H), 1.75-1.50(m, 1H), 1.07-0.80(m, 4H) 1-016; 6.91-6.77(m, 2H), 3.90-3.77(m, 3H), 3.68-3.42(m, 2H), 3.28- 2.48(m, 4H), 2.35-1.80(m, 13H), 1.37(s, 3H), 1.16(s, 3H) 1-017; 7.17-7.05(m, 2H), 7.00-6.90(m, 1H), 6.87-6.78(m, 2H), 6.65- 6.55(m, 2H), 3.87-3.82(m, 3H), 3.56-3.45 and 3.18-2.20 (m, 8H), 2.19-1.70(m, 9H), 1.50-1.38(m, 6H) 1-031; 6.90-6.85(m, 2H), 4.55 and 4.34(s, 2H), 3.88-3.80(m, 3H), 3.30- 2.35(m, 4H), 2.30-1.80(m, 13H), 1.20-1.10(m, 9H) 1-033; 6.90-6.83(m, 2H), 3.84(s, 3H), 3.28-3.15(m, 1H), 3.07-2.96 (m, 1H), 2.90-2.75(m, 2H), 3.40-3.20(m, 6H), 2.06(s, 3H), 2.04 (s, 3H), 1.86(s, 3H), 1.58-1.45(m, 2H), 1.35-1.10(m, 10H), 0.92- 0.83(m, 3H) 1-034; 6.90-6.80(m, 2H), 3.90-3.80(m, 3H), 3.35-3.22(m, 1H), 3.09- 2.98(m, 1H), 2.98-2.70(m, 2H), 2.35-2.20(m, 4H), 2.12-2.00 (m, 6H), 1.92-1.78(m, 6H), 1.48-1.35(m, 6H) 1-035; 6.90-6.82(m, 2H), 3.84(s, 3H), 3.28-3.15(m, 1H), 3.08-2.97 (m, 1H), 2.90-2.75(m, 2H), 2.50-2.20(m, 8H), 2.10-2.02(m, 6 H), 1.86(s, 3H), 1.80-0.70(m, 11H) 1-036; 6.90-6.80(m, 2H), 3.87-3.80(m, 3H), 3.26-3.15(m, 1H), 3.10- 3.00(m, 1H), 2.90-2.78(m, 2H), 2.38-2.13(m, 4H), 2.10-2.00 (m, 6H), 1.86(s, 3H), 1.58-1.40(m, 5H) 1-037; 6.90-6.80(m, 2H), 4.07-3.52(m, 14H), 2.45-2.00(m, 10H), 1.90- 1.84(m, 3H) 1-039; 6.90-6.80(m, 2H), 3.84(s, 3H), 3.25-3.13(m, 1H), 3.12-3.01 (m, 1H), 2.90-2.75(m, 2H), 2.38-2.20(m, 4H), 2.06(s, 3H), 2.05 (s, 3H), 1.84(s, 3H), 1.48-1.35(m, 6H) 1-042; 6.88-6.83(m, 2H), 3.87-3.82(m, 3H), 3.32-2.22(m, 9H), 2.15- 2.03(m, 6H), 1.89-1.85(m, 3H), 1.59-1.47(m, 3H) 1-043; 7.28-7.17(m, 2H), 7.02-6.96(m, 1H), 6.89-6.83(m, 2H), 6.74- 6.60(m, 2H), 4.65 and 4.62(s, 2H), 3.84(s, 3H), 3.29-3.18(m, 1H), 3.12-3.00(m, 1H), 2.92-2.80(m, 2H), 2.40-2.20(m, 4H), 2.10-2.00(m, 6H), 1.90-1.83(m, 3H) 1-044; 7.28-7.17(m, 2H), 6.88-6.83(m, 2H), 6.63-6.48(m, 2H), 4.62 and 4.58(s, 2H), 3.84(s, 3H), 3.70-2.22(m, 8H), 2.03-1.95(m, 6H), 1.86(s, 3H) 1-045; 8.52-8.47(m, 1H), 8.04-7.98(m, 1H), 7.91-7.83(m, 1H), 7.46- 7.38(m, 1H), 6.93-6.85(m, 2H), 4.10(s, 3H), 3.43-3.35(m, 1 H), 3.15-2.90(m, 3H), 2.58-2.48(m, 1H), 2.26(s, 3H), 2.17(s, 3H), 2.11(s, 3H) (Proton peak corresponding to OH was not observed) 1-046; 11.85(brs, 1H), 6.95-6.85(m, 2H), 3.95-3.78(m, 3H), 3.40-2.02 (m, 14H), 1.08-0.70(m, 5H) 1-047; 8.14-7.34(m, 5H), 6.95-6.85(m, 2H), 4.05-3.88(m, 3H), 3.35- 2.00(m, 14H) (Proton peak corresoonding to OH was not observed) 1-048; 11.78-11.65(m, 1H), 7.00-6.83(m, 2H), 3.97-3.80(m, 3H), 3.55- 2.00(m, 15H), 1.25-1.00(m, 6H) 1-051; 7.06-6.98(m, 2H), 6.87-6.80(m, 2H), 6.52-6.44(m, 2H), 3.87- 3.82(m, 3H), 3.62-2.13(m, 8H), 2.08-2.00(m, 6H), 1.87 and 1.82(s, 3H), 1.58-1.40(m, 6H) 1-060; 7.24-7.22(m, 2H), 7.00-6.90(m, 1H), 6.88-6.78(m, 2H), 6.72- 6.60(m, 2H), 4.78-4.65(m, 1H), 3.90-3.76(m, 3H), 3.25-2.96 (m, 2H), 2.89-2.69(m, 2H), 2.35-2.20(m, 4H), 2.10-1.94(m, 6H), 1.88-1.80(m, 3H), 1.55-1.45(m, 3H) 1-063; 7.30-7.15(m, 2H), 7.03-6.94(m, 1H), 6.89-6.82(m, 2H), 6.75- 6.60(m, 2H), 4.67-4.60(m, 2H), 3.88-3.77(m, 3H), 3.33-1.80 (m, 14H), 0.90-0.65(m, 5H) 1-064; 7.40-7.30(m, 1H), 7.12-6.77(m, 4H), 6.53-6.27(m, 1H), 4.77- 4.59(m, 2H), 3.90-2.80(m, 6H), 2.67-2.17(m, 5H), 2.15-1.80 (m, 9H) 1-065; 7.18-7.05(m, 1H), 7.00-6.95(m, 1H), 6.88-6.72(m, 3H), 6.60- 6.42(m, 1H), 4.65-4.53(m, 2H), 3.88-2.45(m, 7H), 2.37-1.85 (m, 13H) 1-067; 7.03-6.68(m, 5H), 6.60-6.38(m, 1H), 4.73-4.65(m, 2H), 3.90- 3.80(m, 6H), 3.75-2.15(m, 8H), 2.10-2.00(m, 6H), 1.90-1.82 (m, 3H) 1-068; 7.15-7.07(m, 1H), 6.90-6.80(m, 2H), 6.60-6.52(m, 1H), 6.43- 6.37(m, 1H), 6.30-6.22(m, 1H), 4.63(s, 2H), 3.83(s, 3H), 3.76 (s, 3H), 3.30-3.20(m, 1H), 3.10-3.00(m, 1H), 2.92-2.80(m, 2H), 2.36-2.23(m, 4H), 2.04(s, 3H), 2.03(s, 3H), 1.54(s, 3H) 1-069; 6.92-6.53(m, 6H), 4.70-4.52(m, 2H), 3.84(s, 3H), 3.76(s, 3H), 3.30-2.10(m, 8H), 2.09-1.95(m, 6H), 1.93-1.82(m, 3H) 1-071; 7.88-7.80(m, 1H), 7.40-7.20(m, 1H), 7.14-7.03(m, 1H), 6.90- 6.82(m, 2H), 6.57-6.50 and 6.37-6.29(m, 1H), 4.78 and 4.74 (s, 2H), 3.87-3.82(m, 3H), 3.70-2.22(m, 8H), 2.14-1.97(m, 6H), 1.90-1.85(m, 3H) 1-072; 7.05-6.97(m, 2H), 6.92-6.85(m, 2H), 6.65-6.50(m, 2H), 4.65- 4.55(m, 2H), 3.90-3.80(m, 3H), 3.29-2.79(m, 4H), 2.38-2.22 (m, 7H), 2.10-2.02(m, 6H), 1.88-1.72(m, 3H) 1-073; 6.93-6.80(m, 4H), 6.67-6.50(m, 2H), 4.65-4.55(m, 2H), 3.84 (s, 3H), 3.28-2.45(m, 4H), 2.35-2.20(m, 4H), 2.10-1.95(m, 6 H), 1.93-1.80(m, 3H) 1-074; 7.35-6.70(m, 6H), 4.67 and 4.64(s, 2H), 3.84(s, 3H), 3.30-2.20 (m, 8H), 2.15-1.95(m, 6H), 1.92-1.85(m, 3H) 1-075; 7.37-6.12(m, 5H), 4.73-4.65(m, 2H), 3.88-3.80(m, 3H), 3.72- 2.20(m, 8H), 2.10-1.95(m, 6H), 1.90-1.82(m, 3H) 1-076; 6.87-6.82(m, 2H), 4.50-4.40(m, 1H), 3.90-3.82(m, 3H), 3.80- 1.40(m, 23H) 1-077; 6.87(s, 2H), 4.25-4.20(m, 2H), 3.90(s, 3H), 3.72(s, 3H), 3.15- 2.90(m, 2H), 2.85-2.70(m, 2H), 2.60-2.50(m, 1H), 2.26(s, 3H), 2.09(s, 6H) 1-079; 9.95-9.87(m, 1H), 7.77-7.68(m, 2H), 6.90-6.65(m, 4H), 4.73 and 4.69(s, 2H), 3.88-3.82(m, 3H), 3.70-2.45(m, 5H), 2.37-1.85 (m, 12H) 1-080; 7.88-7.80(m, 2H), 6.86(brs, 2H), 6.75-6.57(m, 2H), 4.70 and 4.67(s, 2H), 3.84(s, 3H), 3.70-3.58and3.30-2.45(m, 7H), 2.40- 2.22(m, 4H), 2.15-1.95(m, 6H), 1.86(s, 3H) 1-081; 7.33-7.20(m, 2H), 6.86(brs, 2H), 6.58-6.42(m, 2H), 4.61(s, 2 H), 3.84(s, 3H), 3.27-3.17(m, 1H), 3.12-3.00(m, 1H), 2.90-2.79 (m, 2H), 2.37-2.25(m, 4H), 2.02(s, 3H), 2.00(s, 3H), 1.86(s, 3H) 1-082; 7.52-7.40(m, 2H), 6.86(brs, 2H), 6.48-6.30(m, 2H), 4.61 and 4.57(s, 2H), 3.84(s, 3H), 3.27-3.15(m, 1H), 3.12-3.00(m, 1H), 2.90-2.79(m, 2H), 2.35-2.25(m, 4H), 2.05-1.98(m, 6H), 1.86 (s, 3H) 1-083; 7.80-7.70(m, 2H), 7.65-7.58(m, 1H), 7.50-7.30(m, 2H) 7.15- 7.05(m, 1H), 6.92-6.85(m, 1H), 6.80(brs, 2H), 4.77 and 4.75 (s, 2H), 3.82(s, 3H), 3.32-3.20(m, 1H), 3.12-3.00(m, 1H), 2.95- 2.80(m, 2H), 2.35-2.23(m, 4H), 2.08-1.98(m, 6H), 1.86(s, 3H) 1-087; 8.61(s, 1H), 8.06(s, 1H), 7.70-7.61(m, 2H), 7.10-7.05(m, 2H), 6.87-6.65(m, 4H), 4.75-4.69(m, 1H), 3.84(s, 3H)3.28-2.81 (m, 4H)2.40-1.95(m, 10H)1.83(s, 3H), 1.52(m, 3H) 1-088; 6.86(brs, 2H), 6.81-6.78(m, 1H), 3.84(s, 3H), 3.38-3.27(m, 1 H), 3.09-2.98(m, 1H), 2.95-2.80(m, 2H), 2.55-2.45(m, 4H), 2.35- 2.21(m, 4H), 2.10-2.01(m, 6H), 2.00-1.90(m, 2H), 1.86(s, 3H) 1-089; 6.86(brs, 2H), 3.84(s, 3H), 3.40-3.27(m, 1H), 3.10-2.98(m, 1 H), 2.97-2.70(m, 4H), 2.58-2.50(m, 2H), 2.35-2.23(m, 4H), 2.10- 1.86(m, 11H) 1-090; 7.08-6.97(m, 1H), 6.87(brs, 2H), 5.83-5.75(m, 1H), 3.84(s, 3 H), 3.37-3.26(m, 1H), 3.08-2.98(m, 1H), 2.93-2.80(m, 2H), 2.35- 2.10(m, 6H), 2.07(s, 3H), 2.06(s, 3H), 1.86(s, 3H), 1.55-1. 1-091; 7.52-7.49(m, 1H), 7.40(d, J = 15.6 Hz, 1H), 6.87(brs, 2H), 6.68- 6.65(m, 1H), 6.50-6.47(m, 1H), 6.24(d, J = 15.6 Hz, 1H), 3.84 (s, 3H), 3.40-3.29(m, 1H), 3.10-2.99(m, 1H), 2.98-2.81(m, 2 H), 2.35-2.25(m, 4H), 2.09(s, 3H), 2.07(s, 3H), 1.86(s, 3H) 1-092; 6.87(brs, 2H), 4.24 and 4.19(brs, 2H), 3.84(s, 3H), 3.75-2.22 (m, 10H), 2.15-2.02(m, 6H), 1.90-1.85(m, 3H) 1-093; 6.86(brs, 2H), 4.05(s, 2H), 3.84(s, 3H), 3.33(s, 3H), 3.32-3.20 (m, 1H), 3.10-3.00(m, 1H), 2.92-2.80(m, 2H), 2.35-2.23(m, 4 H), 2.10-2.02(m, 6H), 1.87(s, 3H) 1-094; 7.40-7.15(m, 5H), 6.86(brs, 2H), 4.46and4.38(s, 2H), 4.11 and 4.08(s, 2H), 3.84and3.83(s, 3H), 3.78-2.20(m, 8H), 2.06(s, 3 H), 2.04(s, 3H), 1.87(s, 3H) 1-095; 6.88(brs, 2H), 3.84(s, 3H), 3.30-3.18(m, 1H), 3.08-2.98(m, 1 H), 2.92-2.19(m, 2H), 2.35-2.23(m, 4H), 2.10-2.03(m, 6H), 1.98 (s, 3H), 1.86(s, 3H) 1-096; 6.89(brs, 2H), 3.83(s, 3H), 3.28-3.18(m, 1H), 3.08-2.99(m, 1 H), 2.90-2.88(m, 2H), 2.35-2.24(m, 4H), 2.07(s, 3H), 2.06(s, 3H), 1.86(s, 3H), 0.23(s, 9H) 1-098; 6.84(brs, 2H), 4.03(s, 3H), 3.84(s, 3H), 3.39(s, 2H), 3.32-3.20 (m, 1H), 3.12-3.00(m, 1H), 2.95-2.80(m, 2H), 2.37-2.22(m, 4 H), 2.09(s, 3H), 2.08(s, 3H), 1.92(s, 3H), 1.86(s, 3H) 1-099; 6.87-6.80(m, 2H), 3.84 and 3.78(s, 3H), 3.40-2.28(m, 5H), 2.26- 2.22(m, 3H), 2.15-2.08(m, 6H), 1.88 and 1.86(s, 3H) 1-100; 6.85(brs, 2H), 6.32-6.28(m, 1H), 3.84(s, 3H), 3.37-3.28(m, 1 H), 3.16-3.05(m, 1H), 3.00-2.80(m, 2H), 2.50-2.45(m, 3H), 2.40- 2.29(m, 1H), 2.24(s, 3H), 2.11(s, 3H), 2.10(s, 3H), 1.88(s, 3H) 1-101; 6.87(brs, 2H), 3.84(s, 3H), 3.45-3.33(m, 1H), 3.13-2.80(m, 3 H), 2.65(s, 3H), 2.55(s, 3H), 2.37-2.24(m, 4H), 2.10(s, 3H), 2.08 (s, 3H), 1.88(s, 3H) 1-103; 8.31(s, 1H), 6.85(brs, 2H), 3.85(s, 3H), 3.55-3.42(m, 1H), 3.13- 3.03(m, 2H), 2.92-2.83(m, 1H), 2.38-2.18(m, 4H), 2.09(s, 3H), 2.07(s, 3H), 1.89(s, 3H), 1.65-1.50(m, 1H), 1.23-1.17(m, 2H), 1.03-0.97(m, 2H) 1-104; 6.87(brs, 2H), 3.85(s, 3H), 3.70-3.22(m, 10H), 3.08-2.97(m, 1 H), 2.96-2.80(m, 2H), 2.32-2.19(m, 3H), 2.08(s, 3H), 2.05(m, 3H), 1.87(s, 3H) 1-107; 6.86(brs, 2H), 3.84(s, 3H), 3.42-3.31(m, 1H), 3.07-2.72(m, 9 H), 2.31-2.19(m, 4H), 2.09(s, 3H), 2.06(s, 3H), 1.86(s, 3H) 1-108; 7.27(brs, 2H), 3.84(s, 3H), 3.38-3.23(m, 1H), 3.15-2.78(m, 5 H), 2.40-2.01(m, 10H), 1.86(s, 3H), 1.69-1.48(m, 3H), 1.38-1.05 (m, 10H) 1-122; 6.86(brs, 2H), 3.85(s, 3H), 3.39-3.28(m, 1H), 3.11-2.59(m, 9 H), 2.36-1.98(m, 4H), 2.08(s, 3H), 2.06(s, 3H), 1.54(s, 3H) 1-125; 10.06(brs, 1H), 6.99-6.81(m, 2H), 4.66-4.42(m, 2H), 3.50-3.32 (m, 2H), 3.04-1.42(m, 20H) 1-126; 6.86(brs, 2H), 3.84(brs, 3H), 3.58-2.72(m, 12H), 2.35-1.20(m, 16H) 1-127; 7.32-6.62(m, 7H), 4.55-4.28(m, 1H), 3.89-3.79(m, 3H), 3.38- 3.20(m, 1H), 3.02-2.65(m, 3H), 2.29-1.44(m, 13H), 1.13-0.87 (m, 6H) 1-128; 6.97-6.66(m, 6H), 4.57-4.31(m, 1H), 3.84(s, 3H), 3.38-3.23 (m, 1H), 3.04-2.71(m, 3H), 2.30-1.40(m, 13H), 1.17-0.79(m, 6H) 1-129; 6.98-6.43(m, 5H), 4.59-4.40(m, 1H), 3.85(s, 3H), 3.50-3.31 (m, 1H), 3.07-2.76(m, 3H), 2.32-1.50(m, 13H), 1.20-0.81(m, 6H) 1-130; 6.84(brs, 2H), 4.92-4.58(m, 2H), 3.84(s, 3H), 3.82-2.77(m, 9 H), 2.37-1.32(m, 15H), 1.12-0.81(m, 3H) 1-134; 7.50-7.00(m, 5H), 6.85(brs, 2H), 3.85-3.50(m, 5H), 3.20-2.18 (m, 8H), 2.10-1.97(m, 6H), 1.85 and 1.78(s, 3H) 1-139; 7.78-7.57(m, 5H), 6.90-6.82(m, 2H), 4.11(s, 2H), 3.89(s, 3H), 3.85(s, 3H), 3.62-2.20(m, 8H), 2.16-1.85(m, 9H) 1-140; 6.92-6.82(m, 2H), 3.87-3.82(m, 3H), 3.68-3.30(m, 1H), 3.28- 2.00(m, 19H), 1.92-1.84(m, 3H) 1-141: 6.89(brs, 2H), 3.84(s, 3H), 3.38-2.78(m, 8H), 2.40-2.25(m, 4 H), 2.15-1.82(m, 11H) 1-142; 6.88(brs, 2H), 3.85(s, 3H), 3.63-2.22(m, 9H), 2.13-2.02(m, 6 H), 1.90-1.82(m, 3H), 1.28-0.70(m, 4H) 1-143; 6.88(brs, 2H), 3.85(s, 3H), 3.42-2.80(m, 6H), 2.40-1.70(m, 13 H), 0.85-0.72(m, 2H), −0.07(s, 9H) 1-144; 7.45-7.22(m, 5H), 6.86(brs, 2H), 5.13(s, 2H), 3.84(s, 3H), 3.35- 2.22(m, 8H), 2.14-2.00(m, 6H), 1.97-1.80(m, 3H) 1-145; 6.87(brs, 2H), 5.94-5.75(m, 1H), 5.45-5.20(m, 2H), 4.73-4.48 (m, 2H), 3.84(s, 3H), 3.34-3.23(m, 1H), 3.10-2.80(m, 3H), 2.40- 2.22(m, 4H), 2.07(s, 3H), 2.05(s, 3H), 1.86(s, 3H) 1-146; 6.87(brs, 2H), 4.33-4.15(m, 2H), 3.85(s, 3H), 3.62-3.52(m, 2 H), 3.43-3.22(m, 4H), 3.10-2.80(m, 3H), 2.35-2.22(m, 4H), 2.13- 2.01(m, 6H), 1.86(s, 3H) 1-147; 6.87(brs, 2H), 4.33-4.15(m, 2H), 3.85(s, 3H), 3.62-3.52(m, 2 H), 3.43-3.22(m, 4H), 3.10-2.80(m, 3H), 2.35-2.22(m, 4H), 2.13- 2.01(m, 6H), 1.86(s, 3H) 1-148; 7.13-7.08(m, 2H), 6.98-6.92(m, 2H), 6.78(brs, 2H), 3.84(s, 3 H), 3.15-2.96(m, 2H), 2.88-2.67(m, 2H), 2.33-2.19(m, 4H), 1.90 (s, 3H), 1.87(s, 3H), 1.85(s, 3H), 1.47(s, 3H), 1.47(s, 3H) 1-149; 8.10-7.97(m, 2H), 7.75-7.65(m, 2H), 6.86(brs, 2H), 3.85(s, 3 H), 3.45-3.35(m, 1H), 3.18-2.85(m, 3H), 2.42-2.29(m, 1H), 2.25 (s, 3H), 2.13(s, 3H), 2.11(s, 3H), 1.89(s, 3H) 1-150; 6.86(s, 2H), 3.84(s, 3H), 3.47-3.32(m, 3H), 3.29-3.19(m, 2H), 3.07-2.80(m, 3H), 2.32-2.19(m, 4H), 2.09(s, 3H), 2.07(s, 3H), 1.90-1.80(m, 7H) 1-151; 6.86(s, 2H), 3.85(s, 3H), 3.44-3.20(m, 5H), 3.08-2.80(m, 3H), 2.32-2.19(m, 4H), 2.08(s, 3H), 2.06(s, 3H), 1.87(s, 3H), 1.64- 1.37(m, 6H) 1-152; 6.86(s, 2H), 3.84(s, 3H), 3.51-3.28(m, 5H), 3.08-2.80(m, 3H), 2.40-2.18(m, 11H), 2.08(s, 3H), 2.05(s, 3H), 1.86(s, 3H) 1-153; 6.85(brs, 2H), 5.90-5.42(m, 2H), 5.33-4.74(m, 4H), 4.00-3.58 (m, 7H), 3.44-3.30(m, 1H), 3.09-2.80(m, 3H), 2.37-2.18(m, 4H), 2.07(s, 3H), 2.04(s, 3H), 1.87(s, 3H) 1-155: 7.83-7.77(m, 1H), 7.65-7.57(m, 1H), 7.39-7.29(m, 2H), 6.85 (brs, 2H), 3.85(s, 3H), 3.40-3.29(m, 1H), 3.18-3.05(m, 1H), 3.03- 2.84(m, 2H), 2.41-2.28(m, 1H), 2.25(s, 3H), 2.11(s, 3H), 2.09 (s, 3H), 1.88(s, 3H) 1-156; 7.10-6.92(m, 2H), 6.90-6.72(m, 4H), 3.85(s, 3H), 3.80(s, 3H), 3.68-3.53(m, 2H), 3.24-3.12(m, 1H), 3.07-2.74(m, 3H), 2.51- 1.82(m, 13H) 1-159; 7.30-6.67(m, 7H), 3.84(s, 3H), 3.41-3.18(m, 4H), 3.10-2.77 (m, 3H), 2.30-1.66(m, 13H) 1-160; 6.84(brs, 2H), 3.84(s, 3H), 3.79(s, 3H), 3.40-2.82(m, 4H), 2.35- 2.25(m, 1H), 2.25(s, 3H), 2.09(s, 3H), 2.07(s, 3H), 1.87(s, 3 H) 1-161; 7.56(d, J = 8.4 Hz, 2H), 7.20(d, J = 8.4 Hz, 2H), 6.86(brs, 2H), 3.84 (s, 3H), 3.38-2.75(m, 4H), 2.42(s, 3H), 2.41-2.09(m, 1H), 2.25 (s, 3H), 1.92(s, 3H), 1.89(s, 3H), 1.85(s, 3H) 1-162; 7.97(d, J = 8.1 Hz, 1H), 7.75(d, J = 8.1 Hz, 1H), 6.87(brs, 2H), 4.01 (s, 3H), 3.86(s, 3H), 3.42-3.30(m, 1H), 3.20-3.08(m, 4H), 3.05- 2.73(m, 2H), 2.43-2.22(m, 4H), 2.14-2.05(m, 6H), 1.98-1.85 (m, 3H) 1-163; 7.50-7.44(m, 1H), 7.21-7.13(m, 1H), 6.92-6.70(m, 5H), 6.68- 6.55(m, 2H), 4.72-4.59(m, 1H), 3.84(s, 3H), 3.23-2.67(m, 4 H), 2.38-2.16(m, 4H), 2.12-1.80 and 1.62-1.40(m, 12H) 1-164; 11.4(brs, 1H), 7.56-7.10(m, 4H), 6.87-6.82(m, 2H), 3.96-3.85 (m, 3H)3.40-2.65(m, 3H), 2.51-1.97(m, 14H) 1-165; 6.85(brs, 2H), 4.85-4.50(m, 1H), 3.90-3.80(m, 3H), 3.20-2.50 (m, 4H), 2.38-2.00(m, 10H), 1.90-1.83(m, 3H), 1.75-1.35(m, 8H) 1-166; 6.87(brs, 2H), 6.37-6.05(m, 1H), 4.72-4.30(m, 2H), 3.90-3.80 (m, 3H), 3.35-2.55(m, 4H), 2.45-2.03(m, 10H), 1.92-1.85(m, 3H) 2-008; 10.05-10.02(m, 1H), 8.08-7.95(m, 2H), 7.80-7.35(m, 3H), 6.95- 6.85(m, 2H), 5.23-4.78(m, 1H), 4.25-4.05(m, 2H), 3.90-2.00 (m, 12H), 1.30-1.10(m, 3H) 2-010; 7.00-6.85(m, 2H), 4.40-4.25(m, 2H), 4.00-2.02(m, 13H), 1.40- 1.22(m, 3H) (Proton peak corresponding to OH was not observed) 2-015; 10.20-9.95(m, 1H), 8.20-7.98(m, 2H), 7.75-7.45(m, 3H), 7.05- 6.80(m, 2H), 3.97-3.72(m, 1H), 3.60-3.47(m, 1H), 3.32-2.95 (m, 2H), 2.55-2.05(m, 10H) 2-018; 6.84(s, 2H), 3.30-3.20(m, 1H), 3.18-3.07(m, 1H), 3.10-3.00 (m, 1H), 2.82-2.68(m, 2H), 2.25(s, 3H), 2.20(s, 3H), 2.08(s, 3 H), 2.06(s, 3H), 1.08(s, 9H) 3-001; 7.60-7.48 and 6.95-6.80(m, 3H), 4.07-3.85(m, 4H), 3.85-2.50 (m, 3H), 2.35-2.00(m, 9H) 3-002; 6.97-6.83(m, 2H), 3.88(s, 3H), 3.00-2.42(m, 3H), 2.27(s, 3H), 2.15-2.05(m, 6H), 1.86(s, 3H) (Proton peak corresponding to OH was not observed) 4-001; 6.88(s, 2H), 3.84 and 3.82(s, 3H), 2.95-2.71(m, 1H), 2.55-1.96 (m, 17H), 1.10(t, J = 7.5 Hz, 3H) (Proton peak corresponding to OH was not observed) 5-001; 6.88(s, 2H), 2.85-1.99(m, 17H), 1.88-1.78(m, 1H), 1.07(t, J = 7.5 Hz, 3H) (Proton peak corresponding to OH was not observed) 5-002; 6.86(s, 2H), 3.72(s, 3H), 3.01-2.92(m, 1H), 2.72-1.85(m, 17 H), 1.60(t, J = 7.5 Hz, 3H) 6-004; 11.90-11.60(m, 1H), 8.15-7.55(m, 2H), 7.40-7.25(m, 2H), 4.00- 3.80(m, 3H), 3.50-3.35(m, 1H), 3.05-2.55(m, 3H), 2.40-1.90 (m, 10H) 6-005; 11.80-11.60(m, 1H), 8.00-7.00(m, 4H), 4.00-3.80(m, 3H), 3.50- 3.30(m, 1H), 3.05-1.95(m, 12H), 1.20-1.00(m, 3H) 6-006; 11.60-11.45(m, 1H), 7.15-7.05(m, 2H), 3.95-3.85(m, 3H), 3.50- 3.35(m, 1H), 3.00-2.50(m, 3H), 2.50-2.30(m, 2H), 2.30-1.80 (m, 10H), 1.20-1.00(m, 3H) 6-008; 11.60-11.40(m, 1H), 7.25-7.15(m, 2H), 3.95-3.85(m, 3H), 3.50- 3.35(m, 1H), 3.00-2.85(m, 1H), 2.85-2.70(m, 1H), 2.70-2.30 (m, 3H), 2.30-2.18(m, 1H), 2.18-2.05(m, 3H), 2.05-1.95(m, 3H), 1.20-1.00(m, 3H), 0.30-0.10(m, 9H) 6-010; 11.52(brs, 1H), 7.21(brs, 2H), 3.95-3.85(m, 3H), 3.45-3.30(m, 1H), 3.00-2.50(m, 3H), 2.25-1.90(m, 10H), 1.50-1.35(m, 1H), 0.90-0.70(m, 4H) 6-011; 7.21(brs, 2H), 3.85(s, 3H), 3.76(s, 3H), 2.95-2.55(m, 5H), 2.11 (s, 6H), 1.95(s, 3H) 6-012; 7.63-7.55(m, 2H), 7.48-7.40(m, 2H), 7.40-7.25(m, 3H), 3.86 (m, 3H), 3.79(s, 3H), 3.00-2.55(m, 5H), 2.21(s, 6H), 1.95(s, 3 H) 6-013; 7.55-7.40(m, 2H), 7.35-7.17(m, 4H), 3.86(s, 3H), 3.78(s, 3H), 3.00-2.55(m, 5H), 2.38(s, 3H), 2.19(s, 6H), 1.95(s, 3H) 6-014; 7.74-7.63(m, 4H), 7.29(brs, 2H), 3.86(s, 3H), 3.81(s, 3H), 3.03- 2.57(m, 5H), 2.22(s, 6H), 1.96(s, 3H) 6-019; 7.50(d, J = 8.4 Hz, 2H), 7.38(d, J = 8.4 Hz, 2H), 7.25(brs, 2H), 3.86 (s, 3H), 3.80(s, 3H), 3.03-2.57(m, 5H), 2.20(s, 6H), 1.96(s, 3 H) 6-022; 11.61(brs, 1H), 7.07(brs, 2H), 4.05-4.00(m, 2H), 3.91(s, 3H), 3.50- 3.35(m, 1H), 3.20-2.50(m, 7H), 2.30-1.90(m, 10H), 1.60- 1.20(m, 9H), 0.95-0.85(m, 6H) 6-023; 11.74(brs, 1H), 7.73(s, 2H), 3.91(s, 3H), 3.88(s, 3H), 3.55-3.35 (m, 1H), 3.05-2.50(m, 3H), 2.20-1.90(m, 10H) 6-024; 11.58(brs, 1H), 6.97(brs, 2H), 3.90(s, 3H), 3.50-3.30(m, 1H), 3.00- 2.50(m, 3H), 2.44(s, 3H), 2.20-1.90(m, 10H) 6-025; 11.65(brs, 1H), 7.25-7.13(m, 2H), 4.47(s, 2H), 3.91(s, 3H), 3.50- 3.31(m, 1H), 3.02-2.50(m, 3H), 2.41-1.79(m, 10H) 6-026; 11.79(brs, 1H), 7.63(s, 2H), 3.91(s, 3H), 3.53-3.31(m, 1H), 3.02- 1.90(m, 16H) 6-033; 11.38(brs, 1H), 7.20-7.01(m, 2H), 6.34(s, 1H), 3.91(s, 3H), 2.99- 2.50(m, 3H), 2.28-1.90(m, 11H), 1.51(s, 9H) 6-035; 11.63(brs, 1H), 7.57-7.27(m, 5H), 3.92(s, 3H), 3.51-3.38(m, 1 H), 3.03-2.54(m, 3H), 2.32-2.14(m, 7H), 2.01(s, 3H) 6-036; 11.70(brs, 1H), 7.21(brs, 2H), 3.91(s, 3H), 3.47-3.33(m, 1H), 2.99- 2.52(m, 3H), 2.35-1.80(m, 14H), 1.71-1.36(m, 3H) 6-037; 11.00(brs, 1H), 6.78-6.53(m, 2H), 4.05-3.70(m, 6H), 3.50-3.28 (m, 1H), 3.00-2.55(m, 3H), 2.40-1.80(m, 10H) 6-038; 11.61(brs, 1H), 7.32-7.25(m, 1H), 7.03-6.96(m, 1H), 3.91(s, 3 H), 3.53-3.30(m, 1H), 3.05-2.10(m, 10H), 1.99(m, 3H) 6-039; 6.75(brs, 2H), 3.86(s, 3H), 3.74(s, 3H), 2.97-2.83(m, 3H), 2.63- 2.52(m, 1H), 2.25-1.75(m, 2H), 2.09(s, 3H), 2.06(s, 3H), 1.88 (s, 3H), 0.95-0.85(m, 2H), 0.70-0.60(m, 2H) 6-041; 7.40-7.30(m, 2H), 7.15-7.00(m, 3H), 6.70(brs, 2H), 3.87(s, 3 H), 3.80(s, 3H), 3.02-2.85(m, 3H), 2.65-2.2.55(m, 1H), 2.30- 2.15(m, 1H), 2.09(s, 3H), 2.07(s, 3H), 1.89(s, 3H) 6-043; 7.56(d, J = 8.8 Hz, 2H), 7.30-7.20(m, 4H), 3.87(s, 3H), 3.80(s, 3 H), 3.05-2.85(m, 3H), 2.70-2.2.55(m, 1H), 2.25-2.15(m, 1H), 2.22(s, 3H), 2.21(s, 3H), 1.89(s, 3H) 6-045; 7.45-7.25(m, 5H), 6.69(brs, 2H), 5.01(s, 2H), 3.86(s, 3H), 3.76 (s, 3H), 3.00-2.85(m, 3H), 2.65-2.50(m, 1H), 2.25-2.15(m, 1H), 2.10(s, 3H), 2.07(s, 3H), 1.88(s, 3H) 6-046; 8.65-8.55(m, 2H), 7.40-7.30(m, 2H), 6.64(brs, 2H), 5.03(s, 2 H), 3.84(s, 3H), 3.75(s, 3H), 3.00-2.80(m, 3H), 2.65-2.50(m, 1H), 2.25-2.15(m, 1H), 2.16(s, 3H), 2.08(s, 3H), 1.86(s, 3H) 6-047; 8.46(brs, 1H), 7.90-7.80(m, 1H), 7.00-6.90(m, 1H), 6.84(brs, 2H), 3.86(s, 3H), 3.82(s, 3H), 3.05-2.85(m, 3H), 2.70-2.55(m, 1H), 2.30-2.10(m, 1H), 2.13(s, 3H), 2.10(s, 3H), 1.89(s, 3H) 6-051; 8.70-8.66(m, 1H), 7.78-7.60(m, 3H), 7.26-7.17(m, 2H), 3.91 (s, 3H), 3.60-3.35(m, 1H), 3.03-2.91(m, 1H), 2.85-2.55(m, 2 H), 2.35-2.18(m, 7H), 2.00(s, 3H) (Proton peak corresponding to OH was not observed) 6-052; 11.52(brs, 1H), 7.36-7.28(m, 2H), 7.12-7.00(m, 3H), 6.70(brs, 2H), 3.92(s, 3H), 3.46-3.37(m, 1H), 2.95(dd, J = 18.0, 7.5 Hz, 1 H), 2.78(dd, J = 18.0, 2.7 Hz, 1H), 2.61(dd, J = 18.0, 10.8 Hz, 1H), 2.25(dd, J = 18.0, 2.7 Hz, 1H)2.12(s, 3H), 2.10(s, 3H), 1.99(s, 3 H) 6-059; 7.65-7.50(m, 2H), 7.27-7.20(m, 2H), 7.16-7.08(m, 2H), 3.86 (s, 3H), 3.72-3.31(m, 9H), 3.13-2.83(m, 3H), 2.39-2.15(m, 7 H), 1.90(s, 3H) 6-060; 7.56-7.50(m, 2H), 7.23(s, 2H), 7.14-7.06(m, 2H), 3.86(s, 3H) 3.48-3.33(m, 1H), 3.17-2.72(m, 9H), 2.39-2.18(m, 7H), 1.91- 1.87(m, 3H) 6-061; 7.53-7.45(m, 2H), 7.43-7.35(m, 2H), 7.25-7.10(m, 4H), 6.97- 6.88(m, 1H), 6.74-6.62(m, 2H), 4.67and4.64(s, 2H), 3.84(s, 3 H), 3.75-3.65 and 3.34-2.06(m, 11H), 1.87and1.86(s, 3H) 6-062; 7.54-7.47(m, 2H), 7.40-7.34(m, 2H), 7.23(brs, 2H), 3.85(s, 3 H), 3.70-3.27(m, 9H), 3.12-3.01(m, 1H), 2.98-2.82(m, 2H), 2.29 (dd, J = 15.3, 11.1 Hz, 1H), 2.18(s, 3H), 2.16(s, 3H), 1.88(s, 3 H) 6-063; 7.54-7.47(m, 2H), 7.40-7.34(m, 2H), 7.23(brs, 2H), 3.84(s, 3 H), 3.40(dd, J = 18.6, 6.9 Hz, 1H), 3.10-2.80(m, 9H), 2.28(dd, J = 15.3, 11.1 Hz, 1H), 2.18(s, 3H), 2.17(s, 3H), 1.88(s, 3H) 6-064; 7.55-7.24(m, 6H), 3.86(s, 3H), 3.70-2.80(m, 12H), 2.57-2.04 (m, 6H), 1.89(s, 3H), 1.20-1.01(m, 3H) 6-067; 7.01(brs, 2H), 6.31-6.10(m, 2H), 3.84(s, 3H), 3.71(s, 3H), 2.95- 2.80(m, 3H), 2.60-2.50(m, 1H), 2.24-2.05(m, 9H), 1.86(s, 3H), 1.50-1.40(m, 2H), 0.97-0.85(m, 3H) 6-070; 8.50-7.82(m, 2H), 7.38-7.10(m, 2H), 6.65-6.25(m, 2H), 5.05- 4.75(m, 2H), 3.93-3.80(m, 3H), 3.45-1.82(m, 14H) (Proton peak corresponding to OH was not observed) 6-075; 11.45(brs, 1H), 6.90-6.82(m, 2H), 3.89(s, 3H), 3.69-3.33 and 3.05-1.85(m, 17H) 6-077; 11.36(brs, 1H), 7.59-7.34(m, 4H), 7.09-8.87(m, 2H), 4.00-3.78 (m, 6H), 3.54-3.32(m, 1H), 3.09-2.50 and 2.38-1.81(m, 10H) 6-078; 7.58-7.34(m, 4H), 7.03(s, 1H), 6.90-6.86(m, 1H), 3.92-3.22 (m, 15H), 3.09-2.68(m, 3H), 2.40-2.13(m, 4H), 1.88(s, 3H) 6-079; 7.54-7.48(m, 2H), 7.43-7.38(m, 2H), 7.25-7.15(m, 2H), 7.05- 6.68(m, 5H), 4.68(s, 2H), 3.87 and 3.84(s, 3H), 3.75 and 3.73 (s, 3H), 3.41-2.11(m, 8H), 1.90-1.84(m, 3H) 6-080; 7.54-7.48(m, 2H), 7.41-7.35(m, 2H), 7.22(brs, 2H), 3.88-3.82 (m, 3H), 3.58-3.20 and 3.05-2.78 and 2.68-1.70(m, 23H) 6-081; 7.58-7.32(m, 4H), 7.02(brs, 1H), 6.92-6.82(m, 1H), 3.98-3.69 (m, 6H), 3.51-3.26(m, 1H), 3.11-2.73(m, 9H), 2.45-2.12(m, 4H), 1.87(s, 3H) 6-082; 7.66-7.12(m, 6H), 4.04-3.79(m, 3H), 3.39-2.79(m, 4H), 2.43- 1.82(m, 10H), 1.38(s, 9H) 6-083; 8.12-7.91(m, 2H), 7.72-7.16(m, 9H), 5.92-5.58(m, 2H), 3.92- 3.79(m, 3H), 3.42-2.74(m, 4H), 2.52-1.84(m, 10H) 6-086; 7.53-7.48(m, 2H), 7.40-7.36(m, 2H), 7.22(brs, 2H), 3.86(s, 3 H), 3.35-2.25(m, 8H), 2.20-2.12(m, 6H), 1.99-1.96(m, 3H), 1.88 (s, 3H), 1.18-1.12(m, 3H) 6-089; 7.42-7.30(m, 1H), 7. 25-7.12(m, 4H), 3.86(s, 3H), 3.70-3.26 (m, 9H), 3.15-2.79(m, 3H), 2.40-2.11(m, 7H), 1.88(s, 3H) 6-090; 7.51-7.45(m, 1H), 7.32-7.19(m, 2H), 7.09(brs, 2H), 3.86(s, 3 H), 3.70-3.26(m, 9H), 3.12-2.82(m, 3H), 2.36-2.23(m, 1H), 2.17 (s, 3H), 2.14(s, 3H), 1.89(s, 3H) 6-091; 7.29-7.19(m, 2H), 7.03-6.93(m, 1H), 6.85-6.70(m, 2H), 6.67 (brs, 1H), 6.54(brs, 1H), 4.65(s, 2H), 3.84 and 3.83(s, 3H), 3.69- 3.60(m, 3H), 3.38-2.77(m, 3H), 2.65-2.20 and 2.11-1.99 (m, 8H), 1.89-1.79(m, 3H) 6-092; 7.50-7.47(m, 1H), 7.31-6.92(m, 7H), 6.80-6.67(m, 2H), 4.69 (s, 2H), 3.85(s, 3H), 3.37-2.78(m, 4H), 2.40-2.28(m, 1H), 2.15- 2.02(m, 6H), 1.88(s, 3H) 6-093; 7.65-7.57(m, 1H), 7.48-7.38(m, 1H), 7.25-7.15(m, 3H), 3.86 (s, 3H), 3.70-3.30(m, 9H), 3.11-2.82(m, 3H), 2.35-2.24(m, 1 H), 2.18(s, 3H), 2.16(s, 3H), 2.05(s, 3H) 6-094; 6.66(brs, 1H), 6.57-6.52(m, 1H), 3.85and3.84(s, 3H), 3.73-3.27 (m, 13H), 3.09-2.77(m, 3H), 2.39-2.20(m, 3H), 2.12-2.04 (m, 3H), 1.86(s, 3H) 6-095; 6.66(brs, 1H), 6.55(brs, 1H), 3.86and3.84(s, 3H), 3.75-3.65(m, 3H), 3.41-3.18(m, 1H), 3.11-2.02(m, 16H), 1.86(s, 3H) 6-097; 6.63(brs, 2H), 4.13-4.05(m, 2H), 3.85(s, 3H), 3.75-3.68(m, 5 H), 3.43(s, 3H), 2.97-2.82(m, 3H), 2.62-2.50(m, 1H), 2.25-2.13 (m, 1H), 2.09(s, 3H)), 2.06(s, 3H)), 1.88(s, 3H) 6-100; 7.67-7.51(m, 2H), 7.50-7.27(m, 5H), 7.14-6.87(m, 5H), 4.64 (s, 2H), 4.00-3.71(m, 6H), 3.52-3.30(m, 1H), 3.07-1.85(m, 10H) 6-101; 7.82(s, 1H), 7.25(s, 1H), 7.18(s, 1H), 7.09(brs, 2H), 3.87(s, 3H), 3.85(s, 3H), 3.10-2.55(m, 4H), 2.30-2.15(m, 7H), 1.90(s, 3H) 6-105; 8.49-8.40(m, 1H), 7.57-7.27(m, 5H), 7.14(brs, 1H), 3.76-3.65 (m, 3H), 2.80-1.70(m, 14H) 6-108; 11.32(brs, 1H), 6.69-6.47(m, 2H), 4.00-3.71(m, 6H), 3.49-3.31 (m, 1H), 3.00-2.62(m, 3H), 2.41-2.13(m, 4H), 1.97(s, 3H) 6-109; 6.66(brs, 1H), 6.60-6.50(m, 1H), 3.97-3.81(m, 3H), 3.79-3.66 (m, 3H), 3.49-3.22(m, 1H), 3.10-2.68(m, 9H), 2.44-2.19(m, 4H), 2.18-2.02(m, 3H), 1.98-1.80(m, 3H) 6-110; 6.66(m, 1H), 6.57-6.52(m, 1H), 3.85 and 3.84(s, 3H), 3.70 and 3.68(s, 3H), 3.47-3.20(m, 5H), 3.07-2.78(m, 3H), 2.39-2.17 (m, 4H), 2.10 and 2.08(s, 3H), 1.93-1.77(m, 7H) 6-111; 6.66(m, 1H), 6.57-6.50(m, 1H), 3.85 and 3.84(s, 3H), 3.70 and 3.68(s, 3H), 3.50-3.11(m, 5H), 3.06-2.67(m, 3H), 2.38-2.19 (m, 4H), 2.09 and 2.07(s, 3H), 1.97-1.83(m, 3H), 1.67-1.38 (m, 6H) 6-113; 11.85-11.73 and 10.63-10.52 and 9.65-9.35(m, 1H), 7.07- 6.98(m, 1H), 6.92-6.83(m, 1H), 4.33-4.05(m, 1H), 3.93-3.65 (m, 6H), 3.57-1.82(m, 9H), 1.38-0.98(m, 3H) 6-114; 11.60-11.47 and 10.20-10.07 and 7.72-7.37(m, 1H), 6.80- 6.53(m, 2H), 4.43-3.65(m, 6H), 3.58-1.77(m, 13H), 1.40-0.97 (m, 3H) 6-115; 6.70-6.45(m, 2H), 3.88-3.77(m, 3H), 3.70-3.60(m, 3H), 3.48- 2.62(m, 8H), 2.37-2.13(m, 4H), 2.11-1.99(m, 3H), 1.94-1.78 (m, 3H), 1.13-0.82(m, 6H) 6-116; 6.75-6.47(m, 2H), 3.91-3.78(m, 3H), 3.74-3.64(m, 3H), 3.56- 3.19(m, 5H), 3.02-2.41(m, 2H), 2.40-1.81(m, 9H), 1.41-1.00 (m, 8H) 6-117; 6.71-6.48(m, 2H), 3.93-3.62(m, 6H), 3.31-2.70(m, 3H), 2.42- 1.81(m, 11H), 1.21-1.05(m, 9H) 6-118; 8.00-7.94(m, 2H), 7.50-7.41(m, 2H), 6.70-6.63(m, 1H), 6.57- 6.49(m, 1H), 3.91-3.60 (m, 6H), 3.50-3.22(m, 1H), 3.18-2.82 and 2.46-2.09(m, 16H), 1.90-1.85(m, 3H) 6-119; 7.43-7.28(m, 3H), 6.97-6.87(m, 2H), 6.68(brs, 1H), 6.58(brs, 1H), 3.89-3.82(m, 3H), 3.75-3.67(m, 3H), 3.37-2.78(m, 4H), 2.49-2.28(m, 4H), 2.15-2.06(m, 3H), 1.98-1.82(m, 3H) 6-120; 6.71-6.38(m, 3H), 6.19-5.90(m, 2H), 3.91-3.79(m, 3H), 3.73- 3.60(m, 3H), 3.40-3.21(m, 1H), 3.10-2.75 and 2.70-2.20 (m, 7H), 2.17-2.00(m, 3H), 1.97-1.80(m, 3H) 6-121; 8.00-7.90(m, 2H), 7.67-7.53(m, 1H), 7.50-7.37(m, 2H), 6.69- 6.63(m, 1H), 6.57-6.50(m, 1H), 3.91-3.82(m, 3H), 3.69-3.62 (m, 3H), 3.49-3.32(m, 1H), 3.15-2.65(m, 3H), 2.46-2.22(m, 4H), 2.20-2.02(m, 3H), 1.97-1.80(m, 3H) 6-122; 6.67(brs, 1H), 6.55(brs, 1H), 4.72-4.54(m, 2H), 3.91-3.82(m, 3H), 3.78-3.65(m, 3H), 3.40-1.80(m, 17H) 6-123; 6.70-6.47(m, 2H), 4.22-3.50(m, 6H), 3.30-2.40(m, 4H), 2.29 (s, 3H), 2.15-1.79(m, 6H), 1.40-1.02(m, 12H) 6-124; 6.72-6.50(m, 2H), 3.96-3.63(m, 6H), 3.38-2.68 and 2.42-1.25 (m, 23H) 6-125; 6.79-6.53(m, 2H), 4.00-3.62(m, 6H), 3.30-2.65 and 2.40-1.81 (m, 20H) 6-126; 6.67(brs, 1H), 6.56(brs, 1H), 3.98-3.80(m, 3H), 3.79-3.64(m, 3H), 3.58-2.71(m, 6H), 2.69-2.52(m, 2H), 2.42-2.20(m, 4H), 2.19-1.80(m, 8H) 6-127; 6.66(brs, 1H), 6.54(brs, 1H), 3.88-2.83(m, 18H), 2.39-1.77(m, 9H), 1.38-1.02(m, 3H) 7-001; 7.25-7.15(m, 2H), 4.20-4.05(m, 1H), 3.90-3.65(m, 4H), 3.30- 2.00(m, 10H), 1.15-1.00(m, 3H) (Proton peak corresponding to OH was not observed) 7-017; 8.90-8.80(m, 2H), 8.03(brs, 2H), 7.70-7.60(m, 1H), 3.00-2.80 (m, 3H), 2.70-2.60(m, 1H), 2.35-2.25(m, 1H), 2.12(s, 9H) (Proton peak corresponding to OH was not observed) 7-027; 7.02(brs, 1H), 6.88(brs, 1H), 3.91-3.62(m, 3H), 3.51-1.97(m, 12H) 7-030; 9.05(brs, 1H), 6.81-6.55(m, 2H), 3.86-3.81(m, 3H), 3.52-2.53 (m, 3H), 2.52-2.03(m, 11H) 9-003; 7.25-7.19(m, 2H), 7.08(s, 2H), 7.02-6.92(m, 1H), 6.73-6.54 (m, 2H), 4.67-4.57(m, 2H), 3.85-3.77(m, 3H), 3.41-2.38(m, 5 H), 2.24-1.95(m, 10H), 1.17-0.99(m, 6H) 9-004; 11.95(s, 1H), 7.85(s, 1H), 7.59(s, 1H), 7.33(s, 2H), 3.91(s, 3H), 3.50-3.29(m, 2H), 3.03-2.92(m, 1H), 2.87-2.77(m, 1H), 2.50- 2.09(m, 8H), 1.17-1.05(m, 6H) 9-005; 11.79(s, 1H), 7.09(s, 2H), 3.91(s, 3H), 3.50-3.25(m, 2H), 3.10- 2.75(m, 2H), 2.48-2.35(m, 1H), 2.33-2.21(m, 1H), 2.19-2.00 (m, 9H), 1.19-1.05(m, 6H) 9-007; 12.17(s, 1H), 7.85(s, 1H), 7.59(s, 1H), 7.38-7.28(m, 2H), 3.94 (s, 3H), 3.38-3.25(m, 1H), 2.92(dd, J = 17.7, 7.5 Hz, 1H), 2.47- 2.35(m, 1H), 2.30-2.07(m, 8H), 1.10-0.82(m, 5H) 9-012; 7.89(s, 1H), 7.64(s, 1H), 7.32(brs, 2H), 7.23-7.11(m, 2H), 6.99- 6.88(m, 1H), 6.75-6.61(m, 2H), 4.70-4.59(m, 2H), 4.47-4.32 (m, 2H), 3.72-1.83(m, 14H) 9-013; 7.28-7.18(m, 2H), 7.07(brs, 2H), 7.03-6.95(m, 1H), 6.70-6.56 (m, 2H), 4.70-4.63(m, 2H), 4.48-4.32(m, 2H), 3.70-3.56(m, 1H), 3.30-1.82(m, 16H) 9-014; 7.82(s, 1H), 7.59(s, 1H), 7.25(brs, 2H), 4.50-4.25(m, 2H), 3.52- 3.10(m, 1H), 3.03-1.70(m, 12H), 1.17-0.88(m, 6H) 9-018; 11.60(brs, 1H), 7.20(s, 2H), 4.25-4.05(m, 2H), 3.70-3.20(m, 6 H), 3.00-2.70(m, 1H), 2.50-1.80(m, 10H), 1.20-1.00(m, 6H) 9-019; 11.90(brs, 1H), 7.20(brs, 2H), 4.30-4.20(m, 2H), 3.70-3.60(m, 2H), 3.38(s, 3H), 3.35-3.20(m, 1H), 2.90-2.85(m, 1H), 2.55-2.40 (m, 1H), 2.25-2.00(m, 9H), 1.10-0.75(m, 4H) 9-020; 11.95(brs, 1H), 7.86(s, 1H), 7.60(s, 1H), 7.32(brs, 2H), 4.36-4.21 (m, 2H), 3.71-3.59(m, 2H), 3.45-3.22(m, 4H), 3.00-2.86(m, 1H), 2.56-2.04(m, 10H), 1.15-0.69(m, 4H) 9-021; 11.79(s, 1H), 7.09(brs, 2H), 4.32-4.21(m, 2H), 3.70-3.55(m, 2 H), 3.38(s, 3H), 3.35-3.22(m, 1H), 2.96-2.83(m, 1H), 2.52-2.40 (m, 1H), 2.30-2.00(m, 12H), 1.09-0.71(m, 4H) 9-022; 11.67(brs, 1H), 7.86(s, 1H), 7.60(s, 1H), 7.33(brs, 2H), 4.29-4.20 (m, 2H), 3.69-3.40(m, 7H), 3.03-2.75(m, 2H), 2.52-2.08(m, 8H), 1.18-1.01(m, 6H) 9-023; 11.52(brs, 1H), 7.09(brs, 2H), 4.30-4.12(m, 2H), 3.69-3.17(m, 7H), 3.03-2.73(m, 2H), 2.58-1.91(m, 11H), 1.21-0.99(m, 6H) 9-025; 7.58-7.19(m, 6H), 4.50-4.32(m, 2H), 3.72-3.22(m, 9H), 3.14- 2.71(m, 3H), 2.41-1.82(m, 10H) 9-026; 7.61-7.21(m, 6H), 4.56-4.32(m, 2H), 3.49-3.30(m, 1H), 3.19- 2.67(m, 9H), 2.48-1.87(m, 10H) 9-027; 7.57-7.11(m, 8H), 7.02-6.87(m, 1H), 6.75-6.60(m, 2H), 4.70- 4.59(m, 2H), 4.49-4.34(m, 2H), 3.33-1.87(m, 14H) 9-029; 7.07(brs, 2H), 4.75-4.50(m, 2H), 3.10-2.90(m, 6H), 2.85-1.85 (m, 14H) (Proton peak corresponding to OH was not observed) 9-030; 12.00-11.76(m, 1H), 7.21(brs, 2H), 6.04-5.95(m, 1H), 5.87-5.70 (m, 1H), 4.70-4.57(m, 1H), 3.48-3.33(m, 1H), 3.00-2.53 and 2.30-1.49(m, 19H) 11-001; 7.39-7.12(m, 5H), 6.86(brs, 2H), 4.96(s, 2H), 3.81(s, 3H), 3.27- 3.13(m, 1H), 2.61-2.22(m, 6H), 2.06(brs, 6H), 1.87-1.77(m, 3H), 1.26(s, 3H) 12-001; 7.37-7.25(m, 3H), 7.14-7.04(m, 2H), 6.86(brs, 2H), 4.71(s, 2 H), 3.83(s, 3H), 2.88-2.77(m, 2H), 2.47-2.23(m, 5H), 2.15-2.02 (m, 6H), 1.88(s, 3H), 1.37-1.22(m, 3H) 12-002; 11.31(brs, 1H), 6.87(brs, 2H), 3.89(s, 3H), 2.97-1.20(m, 19H) 13-001; 11.60 and 11.57(brs, 1H), 7.09-6.85(m, 2H), 3.96-3.69(m, 6 H), 3.47-3.25(m, 1H), 3.02-2.07(m, 9H), 1.19-1.02(m, 3H) 13-005; 6.66(s, 1H), 6.55(s, 1H), 3.91-2.45 and 2.39-2.00 and 1.97- 1.40(m, 26H), 0.94-0.64(m, 4H) 13-006; 6.64(s, 1H), 6.52(s, 1H), 3.95-3.60(m, 6H), 3.36-2.64(m, 3H), 2.60-2.42(m, 1H), 2.38-2.00(m, 7H), 1.97-1.78(m, 1H), 1.13 (s, 9H), 0.94-0.61(m, 4H) 14-001; 10.53 and 10.48(brs, 1H), 7.10-6.82(m, 2H), 3.82-3.60(m, 3 H), 3.50-3.21 and 3.10-2.79(m, 3H), 2.31-2.07 and 1.31- 0.82(m, 10H) 14-002; 10.05 and 9.99(brs, 1H), 7.10-6.83(m, 2H), 3.84-3.59(m, 3H), 3.39-1.02(m, 13H) 15-001; 10.10-9.96(m, 1H), 6.85-6.52(m, 2H), 4.81-4.60(m, 2H), 3.92- 3.61(m, 3H), 3.53-3.28(m, 1H), 3.04-1.86(m, 14H) 15-002; 10.89-10.70(m, 1H), 6.89-6.51(m, 2H), 6.10-5.84(m, 1H), 5.50- 5.11(m, 2H), 4.76-4.50(m, 2H), 3.93-3.60(m, 3H), 3.50-3.23 (m, 1H), 3.03-1.84(m, 13H) 15-003; 11.22(brs, 1H), 6.78-6.52(m, 2H), 4.00-3.61(m, 5H), 3.50-3.23 (m, 1H), 3.02-2.49(m, 3H), 2.40-1.83(m, 10H), 1.19-1.03 (m, 1H), 0.64-0.47(m, 2H), 0.38-0.18(m, 2H) 15-004; 10.90-10.60 and 8.10-7.60(m, 1H), 6.80-6.55(m, 2H), 4.40- 4.06(m, 2H), 3.90-3.70(m, 3H), 3.70-3.53(m, 2H), 3.37(s, 3 H), 3.03-1.85(m, 14H) 15-005; 6.85-6.50(m, 2H), 4.55-4.32(m, 2H), 3.85-3.67(m, 3H), 3.30- 2.25(m, 8H), 2.20-1.85(m, 6H) (Proton peak corresponding to OH was not observed) 15-006; 8.20-7.95 and 7.15-6.95(m, 1H), 6.80-6.55(m, 2H), 4.69(s, 2H), 3.77(s, 3H), 3.45-2.40(m, 4H), 2.33(s, 3H), 2.20-1.85(m, 7H) 15-007; 6.70-6.52(m, 2H), 4.25-4.15(m, 2H), 3.80-3.22(m, 16H), 3.10- 2.70(m, 4H), 2.40-2.02(m, 7H), 1.95-1.85(m, 3H) 15-008; 6.70-6.48(m, 2H), 4.25-4.00(m, 2H), 3.75-3.60(m, 5H), 3.57- 3.22(m, 6H), 3.20-2.28(m, 11H), 2.20-1.88(m, 6H) 15-009; 6.70-6.48(m, 2H), 4.50-4.35(m, 2H), 3.80-3.63(m, 3H), 3.35- 2.50(m, 4H), 2.48-1.85(m, 10H), 1.15-1.10(m, 9H) 15-010; 6.70-6.50(m, 2H), 4.50-4.30(m, 2H), 3.75-3.65(m, 3H), 3.45- 3.20(m, 1H), 3.10-2.70(m, 8H), 2.45-1.85(m, 10H) 15-011; 6.72-6.55(m, 2H), 4.72-4.65(m, 2H), 3.73(s, 3H), 3.45-2.70 (m, 7H), 2.55-1.90(m, 10H) 15-012; 6.65(brs, 1H), 6.53(brs, 1H), 4.72-4.68(m, 2H), 3.72-3.68(m, 3H), 3.45-2.70(m, 8H), 2.45-1.85(m, 10H), 1.15-0.90(m, 6H) 15-013; 6.66(brs, 1H), 6.55(brs, 1H), 4.69-4.61(m, 2H), 3.84-3.68(m, 6H), 3.40-2.68 and 2.59-2.23 and 2.20-1.88(m, 15H) 15-014; 6.72-6.47(m, 2H), 3.98-3.80(m, 2H), 3.79-3.63(m, 3H), 3.39- 2.60 and 2.41-2.20(m, 7H), 2.17-2.01(m, 4H), 1.98-1.83 (m, 3H), 1.65-1.03(m, 10H), 0.63-0.42(m, 2H), 0.37-0.17(m, 2H) 15-015; 7.39-7.18 and 7.09-6.49(m, 7H), 6.08-5.89(m, 1H), 5.33-5.15 (m, 2H), 4.69-4.48(m, 4H), 3.72-3.61(m, 3H), 3.39-2.72(m, 4H), 2.48-2.21(m, 4H), 2.17-1.80(m, 6H) 15-016; 6.69-6.62(m, 1H), 6.58-6.51(m, 1H), 4.68-4.61(m, 2H), 3.75- 3.66(m, 3H), 3.47-3.18(m, 4H), 3.08-2.72(m, 3H), 2.49-2.21 and 2.13-2.02 and 1.98-1.79(m, 16H) 15-017; 6.70-6.64(m, 1H), 6.58-6.50(m, 1H), 6.09-5.91(m, 1H), 5.35- 5.16(m, 2H), 4.60-4.50(m, 2H), 3.74-3.63(m, 3H), 3.58-3.23 (m, 5H), 3.08-2.76(m, 3H), 2.44-2.18(m, 11H), 2.13-2.03(m, 3H), 1.89(s, 3H) 15-018; 6.70-6.63(m, 1H), 6.58-6.50(m, 1H), 3.92-3.81(m, 2H), 3.78- 3.62(m, 3H), 3.54-2.72(m, 11H), 2.40-2.21(m, 4H), 2.17-2.07 (m, 3H), 1.98-1.82(m, 3H), 1.70-1.05(m, 4H), 0.61-0.46(m, 2H), 0.32-0.20(m, 2H)

Test Example

Subsequently, usefulness of the compound of the present invention as a herbicide will be specifically described in the following Test Examples. The present invention, however, is not limited to these Test Examples.

[Test Example 1] Herbicidal Activity Test by Application Before Weed Generation in Submerged Conditions

After alluvial soil was placed into 1/10000 are of Wagner pot, water was poured and mixed to form a submerged condition having a water depth of 4 cm. Seeds of Echinochloa oryzacola Vasing., Scirpus juncoides, and Monochoria vaginalis were sowed in a mixed manner in the above pot and thereafter 2.5 leaf stage rice plant seedlings were transplanted thereto. On the day of sowing seeds, the emulsion agent of the compound of the present invention prepared in accordance with Formulation Example 2 was diluted with water so as to be a predetermined herbicide amount and the diluted emulsion agent was applied to the surface of the water. The pot was placed in a greenhouse of 25° C. to 30° C. to grow plant. 3 weeks later from the herbicide application, the effect to each plant was investigated in accordance with the following criteria. The results are listed in Table 22.

Criteria

5 Herbicidal ratio of 90% or more (almost completely withered) 4 Herbicidal ratio of 70% or higher and lower than 90% 3 Herbicidal ratio of 40% or higher and lower than 70% 2 Herbicidal ratio of 20% or higher and lower than 40% 1 Herbicidal ratio of 5% or higher and lower than 20% 0 Herbicidal ratio of 5% or lower (almost no effect)

[Test Example 2] Herbicidal Activity Test by Application During Weed Generation in Submerged Conditions

After alluvial soil was placed into 1/10000 are of Wagner pot, water was poured and mixed to form a submerged condition having a water depth of 4 cm. Seeds of Echinochloa oryzacola Vasing., Scirpus juncoides, and Monochoria vaginalis were sowed in a mixed manner in the above pot and the pot was placed in the greenhouse of 25° C. to 30° C. to grow the plants. When Echinochloa oryzacola Vasing., Scirpus juncoides, and Monochoria vaginalis were grown to one leaf stage to two leaf stage, the emulsion agent of the compound of the present invention prepared in accordance with Formulation Example 2 was diluted with water so as to be a predetermined herbicide amount and the diluted emulsion agent was applied to the surface of the water. 3 weeks later from the herbicide application, the effect to each plant was investigated in accordance with the criteria of Test Example 1. The results are listed in Table 23.

[Test Example 3] Herbicidal Effect Test by Foliage Application

After alluvial soil was placed into 1/10000 are of Wagner pot, water was poured and mixed to form a submerged condition having a water depth of 0.1 cm to 0.5 cm. Seeds of Echinochloa crus-galli var. crus-galli, Leptochloa chinensis, Cyperus difformis, and rice were sowed and the pot was placed in the greenhouse of 25° C. to 30° C. to grow the plants. After the plants were grown for 14 days, the emulsion agent of the compound of the present invention prepared in accordance with Formulation Example 2 was diluted with water so as to be a predetermined herbicide amount and the diluted emulsion agent was uniformly applied to a foliage part with a small-size spray. 3 weeks later from the herbicide application, the effect to each plant was investigated in accordance with the criteria of Test Example 1. The results are listed in Table 24.

[Test Example 4] Herbicidal Effect Test by Soil Treatment

Sterilized diluvial soil was placed in a plastic box having a length of 21 cm, a width of 13 cm, and a depth of 7 cm. Each of the seeds of Digitaria ciliaris, Setaria viridis, Echinochloa crus-galli var crus-galli, Avena fatua, Alopecurus myosuroides, Lolium multiorum Lam., Apera spica-venti, Abutilon theophrasti, Amaranthus retroflexus, Chenopodium album, Stellaria media, Galium spurium, Veronica persica, corn, soybean, rice, wheat, beet, and rapeseed was sowed in a spot-like manner and was covered with the soil of a thickness of about 1.5 cm. Subsequently, the emulsion agent of the compound present invention prepared in accordance with Formulation Example 2 was diluted with water so as to be a predetermined herbicide amount and the diluted emulsion agent was uniformly applied to the surface of the soil with a small-size spray. The plastic box was placed in a greenhouse of 25° C. to 30° C. to grow plant. 3 weeks later from the herbicide application, the effect to each plant was investigated in accordance with the criteria of Test Example 1. The results are listed in Table 25.

[Test Example 5] Herbicidal Effect Test by Foliage Application

Sterilized diluvial soil was placed in a plastic box having a length of 21 cm, a width of 13 cm, and a depth of 7 cm. Each of the seeds of Digitaria ciliaris, Setaria viridis, Echinochloa crus-galli var crus-galli, Avena fatua, Alopecurus myosuroides, Lollum multiflorum Lam., Apera spica-venti, Abutilon theophrasti, Amaranthus retroflexus, Chenopodium album, Stellaria media, Galium spurium, Veronica persica, corn, soybean, rice plant, wheat, beet, and rapeseed was sowed in a spot-like manner and was covered with the soil of a thickness of about 1.5 cm. Thereafter, the plants were grown in the greenhouse of 25° C. to 30° C. After the plants were grown for 14 days, the emulsion agent of the compound of the present invention prepared in accordance with Formulation Example 2 was diluted with water so as to be a predetermined herbicide amount and the diluted emulsion agent was uniformly applied to a foliage part with a small-size spray. 3 weeks later from the herbicide application, the effect to each plant was investigated in accordance with the criteria of Test Example 1. The results are listed in Table 26.

The symbols in Table 22 to Table 26 have the following meanings.

A: Echinochloa oryzacola Vasing., B: Scirpus juncoides, C: Monochoria vaginalis, D: Leptochloa chinensis, E: Cyperus iria, F: Digitaria ciliaris, G: Setaria viridis, H: Echinochloa crus-galli var. crus-galli, I: Avena fatua, J: Alopecurus myosuroides, K: Lolium multiflorum Lam., L: Apera spica-venti, M: Abutilon theophrasti, N: Amaranthus retroflexus, O: Chenopodium album, P: Stellaria media, Q: Galium spurium, R: Veronica persica, a: transplanted rice plant, b: directly sowed rice plant, c: corn, d: soybean, e: wheat, f: beet, and g: rapeseed

The application herbicide amount (g/ha) means an amount that a concentration is adjusted so that, when an application amount is converted into per hectare, the herbicide is applied by the number of grams (g) of the described value.

TABLE 22 Application herbicide amount No. (g/ha) A B C a 1-001 320 0 0 0 0 1-002 320 5 4 4 5 1-003 320 5 4 5 5 1-004 320 5 5 4 5 1-005 320 5 5 5 5 1-006 320 5 3 3 4 1-007 320 0 0 0 0 1-008 320 5 3 0 0 1-009 320 0 0 0 0 1-010 320 5 5 2 5 1-011 320 0 0 0 0 1-012 320 0 0 0 0 1-013 320 0 0 0 0 1-014 320 5 5 2 5 1-015 320 5 5 2 5 1-016 320 5 5 4 5 1-017 320 5 5 2 5 1-018 320 5 5 2 5 1-019 320 5 5 2 5 1-020 320 5 5 4 5 1-021 320 0 0 0 0 1-022 320 5 5 2 5 1-023 320 4 0 0 1 1-024 320 5 5 2 5 1-025 320 4 2 0 3 1-026 320 5 5 5 5 1-027 320 4 3 3 4 1-028 320 5 5 1 5 1-029 320 4 0 0 5 1-030 320 2 0 0 1 1-031 320 5 4 2 0 1-032 320 5 5 3 5 1-033 320 5 4 1 5 1-034 320 5 4 2 5 1-035 320 5 5 2 5 1-036 320 5 4 1 5 1-037 320 0 0 0 0 1-038 320 5 5 3 5 1-039 320 5 5 2 5 1-040 320 3 2 0 4 1-041 320 5 5 0 5 1-042 320 5 5 4 5 1-043 320 5 5 2 5 1-044 320 5 5 4 5 1-045 320 5 2 0 3 1-046 320 5 5 4 5 1-047 320 4 0 0 1 1-048 320 5 4 1 5 1-049 320 0 0 0 0 1-050 320 4 2 3 4 1-051 320 5 5 0 5 1-052 320 5 5 0 5 1-053 320 5 3 0 5 1-054 320 5 0 0 5 1-055 320 5 3 0 5 1-056 320 5 5 4 5 1-057 320 5 3 2 4 1-058 320 5 0 0 5 1-059 320 5 3 2 4 1-060 320 5 4 3 5 1-062 320 5 2 1 5 1-063 320 5 3 0 5 1-064 320 5 5 1 4 1-065 320 5 5 0 5 1-066 320 4 0 0 5 1-067 320 5 5 1 5 1-068 320 5 4 3 5 1-069 320 5 4 2 5 1-070 320 4 0 0 4 1-071 320 5 4 0 5 1-072 320 5 4 5 1-073 320 5 5 1 5 1-074 320 5 5 4 5 1-075 320 5 4 5 1-076 192 4 4 0 5 1-077 320 1 2 0 1 1-078 320 5 2 0 5 1-079 320 5 5 3 5 1-080 320 5 5 3 5 1-081 320 5 5 2 5 1-082 320 5 5 2 5 1-083 320 5 4 1 5 1-085 320 4 0 0 3 1-086 320 5 0 0 3 1-087 320 5 5 1 5 1-088 320 5 5 0 5 1-089 320 5 5 3 5 1-090 320 5 5 1 5 1-091 320 5 5 0 4 1-092 320 5 5 0 5 1-093 320 5 5 2 5 1-094 320 5 5 1 5 1-095 320 5 5 2 5 1-096 320 5 5 0 5 1-097 320 3 0 0 3 1-098 320 5 5 4 5 1-099 320 5 4 2 5 1-100 320 5 5 3 5 1-101 320 5 5 2 5 1-102 320 5 3 5 1-103 320 5 5 1 5 1-104 320 5 4 1 3 1-105 320 5 5 4 5 1-106 320 5 3 5 1-107 320 5 4 1 3 1-108 320 5 4 3 5 1-109 320 5 5 3 5 1-110 320 3 0 0 5 1-111 320 5 2 1 5 1-112 320 5 5 5 5 1-113 320 5 4 4 3 1-114 320 5 5 5 5 1-115 320 5 3 4 1 1-116 320 5 4 5 3 1-117 320 5 5 5 5 1-118 320 5 1 2 4 1-119 320 1 0 0 3 1-120 320 4 5 3 0 1-121 320 5 5 3 5 1-122 320 5 5 0 5 1-123 320 5 4 3 5 1-124 320 1 0 0 0 1-125 320 3 0 1 5 1-126 320 4 0 0 3 1-130 320 3 0 0 3 1-131 320 5 4 1 4 1-133 320 4 0 0 1 1-134 320 5 5 1 5 1-135 320 5 5 1 5 1-136 320 5 5 5 5 1-137 320 5 5 5 5 1-138 320 5 5 5 5 1-139 320 5 4 1 5 1-140 320 5 5 1 5 1-142 320 5 5 2 5 1-143 320 4 4 1 5 1-144 320 5 5 3 5 1-145 320 5 5 1 5 1-146 320 5 5 1 5 1-147 320 5 5 1 5 1-148 320 5 4 3 5 1-149 320 5 5 1 5 1-150 320 5 3 0 5 1-151 320 5 3 0 4 1-152 320 4 0 0 2 1-153 320 5 3 0 4 1-154 320 5 4 2 5 1-155 320 5 5 1 5 1-156 320 5 5 1 5 1-159 320 5 0 0 1 1-160 320 5 4 2 5 1-161 320 5 4 1 4 1-162 320 5 4 3 5 1-163 320 5 4 0 5 1-166 320 5 0 0 0 2-001 102 4 0 0 4 2-002 320 0 0 0 0 2-003 320 0 0 0 0 2-005 269 3 0 0 4 2-006 320 5 2 3 3 2-007 320 3 2 0 4 2-008 320 0 0 0 0 2-009 320 0 0 0 0 2-010 320 0 0 0 0 2-011 320 0 0 0 0 2-012 320 0 0 0 0 2-013 320 0 0 0 0 2-014 320 4 3 1 1 2-015 320 0 4 0 0 2-016 320 4 0 0 4 2-017 320 5 5 3 5 2-018 320 5 2 1 4 2-020 320 2 0 0 3 2-021 320 4 4 2 5 2-022 320 1 0 0 3 2-024 320 2 0 0 4 2-025 320 3 0 0 2 2-026 320 3 3 0 4 2-028 320 3 0 0 3 2-030 320 4 0 0 3 2-031 320 4 4 2 5 2-032 320 4 4 1 5 3-001 320 0 0 0 0 3-002 320 0 0 0 0 4-001 320 0 0 0 0 5-001 320 0 0 0 0 5-002 320 0 0 0 0 6-001 320 5 0 0 5 6-002 320 3 0 0 3 6-003 320 5 4 1 5 6-004 320 5 5 2 5 6-005 320 5 5 3 5 6-006 320 5 5 1 5 6-007 320 5 5 1 5 6-008 320 5 5 5 5 6-009 320 5 2 0 3 6-010 320 5 4 1 5 6-015 320 5 5 5 5 6-016 320 5 0 0 4 6-017 320 5 1 0 5 6-018 320 5 5 4 5 6-023 320 0 0 0 4 6-024 320 3 2 3 6-025 320 2 0 0 3 6-026 320 1 0 0 3 6-029 320 5 3 3 5 6-030 320 3 0 0 2 6-031 320 3 0 0 1 6-034 320 5 5 4 5 6-035 320 5 4 1 5 6-037 320 5 5 4 5 6-038 320 5 4 3 5 6-049 320 5 5 4 5 6-050 320 3 1 0 4 6-051 320 4 4 2 5 6-052 320 4 1 0 3 6-053 320 4 2 1 3 6-054 320 1 0 0 2 6-055 320 4 1 0 5 6-056 320 3 0 0 0 6-057 320 3 3 1 5 6-058 320 5 5 5 5 6-059 320 5 5 4 5 6-060 320 5 5 5 5 6-061 320 5 1 1 5 6-062 320 5 4 4 5 6-063 320 5 2 3 4 6-064 320 5 0 0 5 6-065 320 4 2 3 4 6-066 320 5 3 2 3 6-071 320 4 0 0 0 6-072 320 4 0 0 0 6-073 320 4 1 1 5 6-074 320 1 0 0 2 6-075 320 4 1 2 3 6-076 320 5 3 2 5 6-077 320 5 3 3 5 6-078 320 5 5 4 5 6-079 320 4 0 2 5 6-080 320 5 1 2 5 6-081 320 5 0 1 3 6-082 320 5 4 4 5 6-083 320 5 4 4 5 6-084 320 5 3 0 5 6-085 320 5 3 0 5 6-086 320 5 2 0 5 6-087 320 5 0 0 2 6-088 320 4 1 0 3 6-089 320 5 3 3 5 6-090 320 5 0 0 0 6-091 320 5 5 4 5 6-092 320 3 0 0 0 6-093 320 5 5 4 5 6-094 320 5 5 3 5 6-095 320 5 4 0 5 6-096 320 1 0 0 5 6-098 320 0 1 0 1 6-099 320 5 5 5 5 6-100 320 5 5 5 5 6-103 320 5 0 0 5 6-104 320 5 5 5 5 6-106 320 5 5 4 5 6-107 320 5 5 5 5 6-108 320 4 3 0 5 6-109 320 5 3 3 5 6-110 320 5 3 0 5 6-111 320 5 5 2 5 6-112 320 5 0 0 4 6-113 320 4 0 0 5 7-001 320 0 0 0 0 7-002 320 0 0 0 2 7-003 320 5 0 0 0 7-004 320 5 3 0 5 7-005 320 3 0 0 1 7-006 320 3 0 0 2 7-007 320 5 1 3 5 7-008 320 4 2 0 5 7-010 320 5 5 1 5 7-011 320 2 1 0 1 7-012 320 3 0 0 1 7-015 320 5 1 2 5 7-018 320 2 0 0 2 7-019 320 1 0 0 0 7-020 320 2 0 0 2 7-022 320 4 2 3 3 7-023 320 2 0 0 1 7-024 320 2 1 2 2 7-026 320 3 0 0 0 7-027 320 4 0 2 3 7-029 320 2 0 0 0 8-001 320 0 0 0 0 8-002 320 0 0 0 0 8-003 320 0 0 0 0 9-001 320 4 0 0 4 9-002 320 5 2 0 5 9-003 320 5 4 1 5 9-004 320 5 2 0 5 9-005 320 4 0 0 4 9-006 320 5 4 0 5 9-007 320 5 4 0 5 9-008 320 5 5 4 5 9-009 320 4 0 0 5 9-010 320 5 5 4 5 9-011 320 5 5 4 5 9-012 320 5 4 2 5 9-013 320 5 5 1 5 9-014 320 5 4 2 5 9-015 320 5 5 1 5 9-016 320 5 5 2 5 9-017 320 4 2 0 4 9-018 320 1 0 0 2 9-019 320 4 0 0 4 9-020 320 5 4 1 5 9-021 320 5 5 2 5 9-022 320 5 3 0 5 9-023 320 5 5 4 5 9-024 320 5 4 2 5 9-025 320 5 1 1 0 9-026 320 4 0 0 0 9-027 320 5 2 1 5 9-028 320 5 5 5 5 10-002 320 1 0 0 1 10-003 320 1 0 0 3 10-004 320 5 0 0 5 11-002 320 2 0 0 2 12-002 320 5 3 2 3 13-001 320 5 2 0 5 13-002 320 5 4 0 5 13-003 320 5 5 0 5 13-004 320 5 5 5 5 13-005 320 5 0 2 5 13-006 320 5 5 4 5 14-001 320 4 3 3 5 14-002 320 4 1 2 2

TABLE 23 Application herbicide amount No. (g/ha) A B C 1-001 320 0 0 0 1-002 320 5 3 3 1-003 320 5 3 3 1-004 320 5 4 4 1-005 320 5 4 4 1-006 320 5 3 3 1-007 320 0 0 0 1-008 320 5 2 0 1-009 320 0 0 0 1-010 320 5 5 2 1-011 320 0 0 0 1-012 320 0 0 0 1-013 320 0 0 0 1-014 320 5 3 3 1-015 320 5 4 4 1-016 320 5 4 3 1-017 320 5 4 3 1-018 320 5 5 3 1-019 320 5 5 2 1-020 320 5 3 2 1-021 320 0 0 0 1-022 320 4 5 3 1-023 320 4 0 0 1-024 320 5 5 3 1-025 320 1 0 0 1-026 320 5 3 3 1-027 320 4 3 0 1-028 320 5 4 0 1-029 320 4 0 0 1-030 320 2 0 0 1-031 320 5 2 0 1-032 320 5 4 3 1-033 320 5 4 2 1-034 320 5 3 3 1-035 320 5 4 4 1-036 320 5 4 2 1-037 320 0 0 0 1-038 320 5 5 4 1-039 320 5 5 3 1-040 320 4 0 0 1-041 320 5 0 0 1-042 320 5 4 3 1-043 320 5 5 3 1-044 320 5 4 3 1-045 320 3 0 0 1-046 320 5 5 3 1-047 320 2 0 0 1-048 320 5 4 2 1-049 320 0 0 0 1-050 320 3 0 0 1-051 320 5 5 3 1-052 320 5 2 0 1-053 320 4 0 0 1-054 320 3 0 0 1-055 320 2 0 0 1-056 320 5 5 4 1-057 320 2 0 0 1-058 320 5 0 0 1-059 320 4 0 0 1-060 320 5 4 0 1-062 320 3 0 0 1-063 320 4 2 0 1-064 320 5 4 1 1-065 320 4 5 0 1-066 320 2 0 0 1-067 320 4 4 2 1-068 320 5 5 3 1-069 320 4 4 3 1-070 320 4 0 0 1-071 320 5 3 1-072 320 5 3 0 1-073 320 5 5 2 1-074 320 5 4 1-075 320 5 4 1-076 192 5 4 0 1-078 320 4 0 0 1-079 320 5 4 3 1-080 320 4 4 2 1-081 320 5 4 3 1-082 320 5 5 3 1-083 320 5 4 3 1-085 320 3 0 0 1-086 320 5 0 1-087 320 5 5 1 1-088 320 5 5 3 1-089 320 5 4 3 1-090 320 5 5 3 1-091 320 5 3 0 1-092 320 5 4 0 1-093 320 5 5 3 1-094 320 5 5 4 1-095 320 5 4 1 1-096 320 5 5 1-097 320 1 0 0 1-098 320 5 4 3 1-099 320 4 4 2 1-100 320 5 5 3 1-101 320 5 5 2 1-102 320 5 2 2 1-103 320 5 4 0 1-104 320 5 4 0 1-105 320 5 5 3 1-106 320 5 0 0 1-107 320 5 2 0 1-108 320 5 3 1 1-109 320 5 5 2 1-110 320 2 0 0 1-111 320 5 1 0 1-112 320 4 4 4 1-113 320 3 3 0 1-114 320 4 3 4 1-115 320 3 2 0 1-116 320 2 3 2 1-117 320 4 3 3 1-118 320 2 0 1-120 320 1 5 3 1-121 320 5 4 1 1-122 320 5 5 0 1-123 320 5 3 2 1-124 320 2 0 0 1-125 320 2 0 0 1-130 320 1 0 0 1-131 320 4 4 0 1-133 320 1 0 0 1-134 320 5 4 3 1-135 320 5 4 0 1-136 320 4 4 5 1-137 320 4 4 3 1-138 320 3 4 2 1-139 320 5 4 1 1-140 320 5 5 3 1-142 320 5 4 1-143 320 4 4 3 1-144 320 5 4 2 1-145 320 5 5 3 1-146 320 5 5 4 1-147 320 5 5 3 1-148 320 5 4 4 1-149 320 5 4 3 1-150 320 5 3 1 1-151 320 5 1 2 1-152 320 2 0 0 1-153 320 4 1 0 1-154 320 5 4 4 1-155 320 5 5 3 1-156 320 5 5 3 1-159 320 4 1 3 1-160 320 5 4 4 1-161 320 5 4 3 1-162 320 5 1 2 1-163 320 5 4 3 1-166 320 3 0 0 2-001 102 0 0 0 2-002 320 0 0 0 2-003 320 0 0 0 2-005 269 3 0 0 2-006 320 5 2 2 2-007 320 3 0 0 2-008 320 0 0 0 2-009 320 0 0 0 2-010 320 0 0 0 2-011 320 0 0 0 2-012 320 0 0 0 2-013 320 0 0 0 2-014 320 4 3 0 2-015 320 0 0 0 2-016 320 4 0 0 2-017 320 5 4 4 2-018 320 4 0 0 2-020 320 1 0 0 2-021 320 5 2 1 2-022 320 1 0 0 2-024 320 1 0 0 2-026 320 4 3 0 2-028 320 3 0 0 2-030 320 3 0 0 2-031 320 4 0 0 2-032 320 4 1 0 3-001 320 0 0 0 3-002 320 0 0 0 4-001 320 0 0 0 5-001 320 0 0 0 5-002 320 0 0 0 6-001 320 4 0 0 6-002 320 0 0 0 6-003 320 4 1 3 6-004 320 5 4 6-005 320 5 2 3 6-006 320 5 5 1 6-007 320 5 3 2 6-008 320 5 5 5 6-009 320 3 0 0 6-010 320 5 3 0 6-015 320 5 5 5 6-016 320 3 0 0 6-017 320 4 3 0 6-018 320 5 4 3 6-024 320 1 0 0 6-025 320 2 0 0 6-029 320 5 3 2 6-030 320 2 0 0 6-031 320 4 0 0 6-034 320 5 5 3 6-035 320 5 4 0 6-036 320 3 0 0 6-037 320 5 4 4 6-038 320 4 4 1 6-049 320 5 4 3 6-050 320 3 0 0 6-051 320 5 4 2 6-052 320 3 0 0 6-053 320 3 1 2 6-054 320 2 1 0 6-055 320 5 2 0 6-056 320 1 0 0 6-057 320 3 2 0 6-058 320 5 5 5 6-059 320 5 4 4 6-060 320 5 4 4 6-061 320 5 4 2 6-062 320 5 3 3 6-063 320 2 3 2 6-064 320 4 0 0 6-065 320 5 1 2 6-066 320 5 0 0 6-071 320 2 0 0 6-072 320 1 0 0 6-073 320 4 2 1 6-074 320 1 0 0 6-075 320 1 0 1 6-076 320 5 1 1 6-077 320 5 4 3 6-078 320 4 2 3 6-079 320 3 2 3 6-080 320 5 4 3 6-081 320 1 0 0 6-082 320 4 3 5 6-083 320 5 3 4 6-084 320 4 3 0 6-085 320 5 4 1 6-086 320 4 4 3 6-087 320 2 0 0 6-088 320 4 2 0 6-089 320 5 2 3 6-090 320 3 0 0 6-091 320 5 5 3 6-092 320 1 0 0 6-093 320 5 3 3 6-094 320 5 2 1 6-095 320 5 3 2 6-096 320 4 0 0 6-099 320 5 5 5 6-100 320 5 5 5 6-103 320 5 0 0 6-104 320 5 5 5 6-106 320 5 5 4 6-107 320 5 5 5 6-108 320 4 1 2 6-109 320 5 2 2 6-110 320 5 1 0 6-111 320 5 3 4 6-112 320 3 0 0 6-113 320 5 0 3 7-001 320 0 0 0 7-002 320 0 0 0 7-003 320 2 0 0 7-004 320 4 0 0 7-005 320 1 0 0 7-006 320 2 0 0 7-007 320 5 0 3 7-008 320 4 0 0 7-010 320 5 5 1 7-011 320 3 2 0 7-012 320 3 0 0 7-013 320 2 0 0 7-015 320 5 0 0 7-018 320 1 0 0 7-020 320 1 0 0 7-024 320 1 0 0 7-027 320 3 0 2 7-031 320 0 1 2 8-001 320 0 0 0 8-002 320 0 0 0 8-003 320 0 0 0 9-001 320 4 0 0 9-002 320 5 0 0 9-003 320 5 4 9-004 320 5 2 0 9-005 320 3 0 0 9-006 320 5 4 9-007 320 5 4 9-008 320 5 4 3 9-009 320 2 0 0 9-010 320 4 4 1 9-011 320 5 5 4 9-012 320 5 4 2 9-013 320 5 5 3 9-014 320 2 0 0 9-015 320 5 3 9-016 320 5 4 1 9-017 320 1 0 0 9-018 320 1 0 0 9-019 320 3 0 0 9-020 320 4 4 0 9-021 320 5 5 9-022 320 4 0 0 9-023 320 5 4 1 9-024 320 3 3 1 9-027 320 3 0 0 9-028 320 5 4 4 9-029 320 0 0 0 10-002 320 1 0 0 10-003 320 3 0 0 10-004 320 5 0 0 11-002 320 2 0 0 12-002 320 5 3 1 13-001 320 5 0 0 13-002 320 5 5 2 13-003 320 5 4 3 13-004 320 5 5 4 13-005 320 5 2 13-006 320 5 3 4 14-001 320 5 0 1 14-002 320 5 0 0

TABLE 24 Application herbicide amount No. (g/ha) H D E b 1-001 320 0 0 0 0 1-002 320 5 5 5 5 1-003 320 5 5 5 5 1-004 320 5 5 5 5 1-005 320 5 5 5 5 1-006 320 5 5 5 5 1-007 320 0 5 0 0 1-008 320 5 5 4 5 1-009 320 0 0 0 0 1-010 320 5 5 5 5 1-011 320 0 5 0 0 1-012 320 0 0 0 0 1-013 320 0 2 0 0 1-014 320 5 5 5 5 1-015 320 5 5 5 5 1-016 320 5 5 5 5 1-017 320 5 5 5 5 1-018 320 5 5 3 5 1-019 320 5 5 5 5 1-020 320 5 5 2 5 1-021 320 2 0 0 0 1-022 320 5 5 4 5 1-023 320 5 5 0 4 1-024 320 5 5 5 5 1-025 320 5 5 5 5 1-026 320 5 5 5 5 1-027 320 5 5 5 5 1-028 320 5 5 5 5 1-029 320 5 5 4 5 1-030 320 5 5 3 5 1-031 320 3 4 0 5 1-032 320 5 5 5 5 1-033 320 5 5 5 5 1-034 320 5 5 5 5 1-035 320 5 5 5 5 1-036 320 5 5 5 5 1-037 320 0 0 0 0 1-038 320 5 5 5 5 1-039 320 5 5 5 5 1-040 320 5 4 4 5 1-041 320 5 5 5 5 1-042 320 5 5 5 5 1-043 320 5 5 5 5 1-044 320 5 5 5 5 1-045 320 5 4 0 3 1-046 320 5 5 5 5 1-047 320 1 3 0 2 1-048 320 5 4 5 5 1-049 320 0 0 0 0 1-050 320 5 4 5 5 1-051 320 5 5 5 5 1-052 320 5 5 5 5 1-053 320 5 5 4 5 1-054 320 5 5 0 5 1-055 320 5 5 4 5 1-056 320 5 5 5 5 1-057 320 4 3 3 5 1-058 320 5 5 5 5 1-059 320 4 1 3 5 1-060 320 5 5 5 5 1-062 320 4 3 4 5 1-063 320 5 5 5 5 1-064 320 5 5 5 5 1-065 320 5 5 5 5 1-066 320 5 2 5 5 1-067 320 5 5 5 5 1-068 320 5 5 5 5 1-069 320 5 5 5 5 1-070 320 5 4 4 5 1-071 320 5 5 5 5 1-072 320 4 5 4 5 1-073 320 5 5 5 5 1-074 320 5 5 5 5 1-075 320 5 5 5 5 1-076 192 5 5 5 5 1-078 320 5 4 0 5 1-079 320 5 5 5 5 1-080 320 5 5 5 5 1-081 320 5 5 5 5 1-082 320 5 5 5 5 1-083 320 5 5 5 5 1-084 320 2 0 0 1 1-085 320 5 4 0 5 1-086 320 5 4 4 5 1-087 320 5 5 5 5 1-088 320 5 5 5 5 1-089 320 5 5 5 5 1-090 320 5 5 5 5 1-091 320 5 5 5 5 1-092 320 5 5 5 5 1-093 320 5 5 5 5 1-094 320 5 5 4 5 1-095 320 5 5 5 5 1-096 320 5 5 5 5 1-098 320 5 5 5 5 1-099 320 5 5 5 5 1-100 320 5 5 5 5 1-101 320 5 5 5 5 1-102 320 5 5 5 5 1-103 320 5 5 5 5 1-104 320 5 5 5 5 1-105 320 5 5 5 5 1-106 320 5 5 5 5 1-107 320 5 5 5 5 1-108 320 5 5 5 5 1-109 320 5 5 5 5 1-110 320 5 5 5 5 1-111 320 5 5 5 5 1-112 320 5 5 5 5 1-114 320 5 5 2 5 1-116 320 5 3 4 5 1-117 320 5 4 5 5 1-118 320 4 0 0 5 1-119 320 5 4 0 5 1-120 320 5 0 4 3 1-121 320 5 5 4 5 1-122 320 5 5 5 5 1-123 320 5 5 4 5 1-124 320 5 5 0 5 1-125 320 5 5 2 5 1-126 320 3 5 2 5 1-130 320 4 5 4 5 1-131 320 5 5 5 5 1-132 320 2 1 0 1 1-133 320 3 0 0 0 1-134 320 5 5 5 5 1-135 320 5 4 5 1-136 320 5 2 5 1-137 320 5 5 5 1-138 320 3 2 5 1-139 320 5 5 5 5 1-140 320 5 5 5 1-141 320 2 0 1 1-142 320 5 5 5 1-143 320 4 4 5 1-144 320 5 5 5 1-145 320 5 5 5 1-146 320 5 5 5 1-147 320 5 5 5 1-148 320 5 5 4 5 1-149 320 5 5 5 5 1-150 320 5 4 5 1-151 320 4 4 5 1-152 320 5 5 5 5 1-153 320 5 5 4 5 1-154 320 5 5 5 5 1-155 320 5 5 5 5 1-156 320 5 5 5 5 1-157 320 0 4 0 1-158 320 0 2 0 2 1-159 320 4 5 4 5 1-160 320 5 5 5 5 1-161 320 4 5 4 5 1-162 320 5 5 5 5 1-163 320 5 5 5 5 1-164 320 2 3 0 4 1-166 320 4 4 3 2-001 102 5 5 5 5 2-002 320 0 0 0 0 2-003 320 5 5 4 4 2-005 269 5 5 4 5 2-006 320 5 5 5 5 2-007 320 5 5 5 5 2-008 320 0 0 0 0 2-009 320 3 0 0 1 2-010 320 3 0 0 1 2-011 320 0 0 0 0 2-012 320 0 0 0 0 2-013 320 0 0 0 0 2-014 320 5 4 5 5 2-015 320 1 0 0 4 2-016 320 5 5 4 5 2-017 320 5 5 5 5 2-018 320 5 5 5 5 2-020 320 2 2 0 2 2-021 320 5 3 3 5 2-022 320 1 4 2 5 2-024 320 5 3 0 5 2-025 320 3 1 0 4 2-026 320 5 4 5 5 2-027 320 3 0 0 5 2-028 320 5 5 4 5 2-029 320 0 0 0 4 2-030 320 4 5 0 5 2-031 320 5 5 5 5 2-032 320 5 3 4 5 3-001 320 3 2 0 2 3-002 320 0 0 0 0 4-001 320 2 3 0 4 5-001 320 2 3 0 5 5-002 320 0 0 0 0 6-001 320 5 5 0 5 6-002 320 4 4 0 5 6-003 320 5 5 5 5 6-004 320 5 5 5 5 6-005 320 5 5 3 5 6-006 320 5 5 5 5 6-007 320 5 5 5 5 6-008 320 5 5 5 5 6-009 320 5 5 0 5 6-010 320 5 5 5 5 6-015 320 5 5 5 5 6-016 320 5 5 1 5 6-017 320 5 5 4 5 6-018 320 5 5 5 5 6-023 320 5 5 4 5 6-024 320 3 2 3 3 6-025 320 5 5 4 5 6-026 320 5 5 5 5 6-027 320 2 3 0 0 6-029 320 5 5 5 5 6-030 320 4 5 0 2 6-031 320 3 2 2 4 6-033 320 0 0 3 0 6-034 320 5 5 4 5 6-035 320 5 5 5 5 6-036 320 4 5 3 4 6-037 320 5 5 5 5 6-038 320 5 5 5 5 6-049 320 5 5 5 5 6-050 320 5 5 5 5 6-051 320 5 5 5 5 6-052 320 5 5 3 5 6-053 320 5 5 3 5 6-054 320 5 5 3 5 6-055 320 5 5 5 5 6-056 320 4 5 3 5 6-057 320 5 5 5 5 6-058 320 5 5 5 5 6-059 320 5 5 5 5 6-060 320 5 5 5 5 6-061 320 5 5 5 5 6-062 320 5 5 5 5 6-063 320 4 5 1 5 6-064 320 5 5 0 4 6-065 320 5 5 5 5 6-066 320 5 5 5 5 6-068 320 0 2 0 0 6-070 320 0 4 0 0 6-071 320 4 5 0 1 6-072 320 5 5 0 0 6-073 320 5 5 5 5 6-074 320 4 5 2 1 6-075 320 3 3 3 4 6-076 320 5 5 5 5 6-077 320 5 5 5 5 6-078 320 5 5 0 5 6-079 320 5 5 4 5 6-080 320 5 5 5 5 6-081 320 1 3 0 0 6-082 320 5 5 5 5 6-083 320 5 5 5 5 6-084 320 5 5 5 5 6-085 320 5 5 5 5 6-086 320 5 5 5 5 6-087 320 5 5 0 5 6-088 320 5 5 5 5 6-089 320 5 5 4 5 6-090 320 0 5 0 0 6-091 320 5 5 5 5 6-092 320 5 5 4 5 6-093 320 5 5 4 5 6-094 320 5 5 5 5 6-095 320 5 5 5 5 6-096 320 5 4 5 5 6-098 320 3 5 4 5 6-099 320 5 5 5 5 6-100 320 5 5 5 5 6-103 320 5 5 5 5 6-104 320 5 5 5 6-105 320 3 4 4 6-106 320 4 5 5 6-107 320 5 5 5 6-108 320 5 5 5 6-109 320 5 4 5 6-110 320 5 5 5 6-111 320 5 5 5 6-112 320 5 5 4 5 6-113 320 5 5 5 5 7-001 320 4 5 0 2 7-002 320 5 5 3 5 7-003 320 5 5 0 5 7-004 320 5 5 5 5 7-005 320 5 5 0 5 7-006 320 5 5 0 5 7-007 320 5 5 4 5 7-008 320 5 5 5 5 7-010 320 5 5 5 5 7-011 320 5 4 5 5 7-012 320 5 5 4 5 7-014 320 4 5 2 5 7-015 320 5 5 5 5 7-016 320 0 5 0 0 7-017 320 5 5 4 5 7-018 320 3 5 3 3 7-019 320 5 4 2 3 7-020 320 4 5 3 4 7-021 320 2 2 0 0 7-022 320 0 4 0 0 7-023 320 0 5 0 0 7-024 320 5 5 2 3 7-025 320 1 3 0 0 7-026 320 0 3 0 0 7-027 320 5 5 4 5 7-028 320 0 0 0 0 7-029 320 3 4 0 0 7-031 320 4 5 3 5 8-001 320 0 0 0 0 8-002 320 0 0 0 0 8-003 320 0 0 0 0 9-001 320 5 4 2 5 9-002 320 5 5 5 5 9-003 320 5 5 5 5 9-004 320 5 5 5 5 9-005 320 5 5 2 4 9-006 320 5 5 5 5 9-007 320 5 5 5 5 9-008 320 5 5 5 5 9-009 320 5 5 4 5 9-010 320 5 5 5 5 9-011 320 5 5 5 5 9-012 320 5 5 5 5 9-013 320 5 5 5 5 9-014 320 5 5 5 5 9-015 320 5 5 5 5 9-016 320 5 5 5 5 9-017 320 5 5 3 5 9-018 320 2 0 0 4 9-019 320 5 5 4 5 9-020 320 5 5 5 5 9-021 320 5 5 5 5 9-022 320 5 5 5 5 9-023 320 5 5 5 5 9-024 320 5 5 5 5 9-025 320 0 5 0 2 9-026 320 0 3 0 0 9-027 320 5 5 5 3 9-028 320 5 5 5 9-029 320 4 4 3 10-001 320 5 4 0 3 10-002 320 5 5 3 5 10-003 320 5 4 0 5 10-004 320 5 5 5 5 11-002 320 5 5 4 5 12-002 320 5 5 5 5 13-001 320 5 5 4 5 13-002 320 5 5 5 5 13-003 320 5 5 5 5 13-004 320 5 5 5 5 13-005 320 5 5 5 5 13-006 320 5 5 5 5 14-001 320 5 5 5 5 14-002 320 5 5 5 5

TABLE 25 Application herbicide amount No. (g/ha) F G H I J K L M N O P Q R b c d e f g 1-001 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1-002 320 5 5 5 5 5 5 5 5 5 5 3 1 5 5 4 0 4 5 5 1-003 320 5 5 5 4 5 5 5 4 3 3 0 5 5 3 5 2 4 1-004 320 5 5 5 5 5 5 5 5 5 0 0 0 5 4 3 3 4 4 1-005 320 5 5 5 5 5 5 5 5 5 0 0 0 5 4 2 4 4 4 1-006 320 5 4 5 3 4 5 5 4 4 0 0 0 0 5 1 0 0 0 0 1-007 320 0 0 0 0 0 2 3 0 0 0 0 0 0 0 1-008 320 5 4 4 0 5 5 5 0 0 3 0 0 0 0 1-009 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1-010 320 5 5 5 5 5 5 5 5 5 4 2 4 5 4 4 4 4 4 1-011 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1-012 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1-013 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1-014 320 5 5 5 5 5 5 5 4 5 4 4 4 1-015 320 5 5 5 5 5 5 5 5 5 3 5 4 3 3 4 1-016 320 5 5 5 5 5 5 5 5 5 5 4 3 2 0 4 1-017 320 5 5 5 5 5 5 5 5 5 5 4 2 2 0 4 1-018 320 5 5 5 4 5 5 5 4 2 5 4 0 4 0 4 1-019 320 5 5 5 5 5 5 5 4 3 5 4 3 3 0 4 1-020 320 5 5 5 4 5 5 5 3 0 0 0 5 1 0 2 0 4 1-021 320 0 0 0 0 0 2 0 0 0 0 0 2 0 0 0 0 0 1-022 320 5 5 5 4 5 5 5 0 0 5 0 0 4 3 1-023 320 4 3 3 0 0 3 4 0 0 0 0 0 5 0 0 0 0 0 1-024 320 5 5 5 4 5 5 5 3 4 0 5 1 1 4 0 3 1-025 320 5 5 5 3 4 5 5 0 0 0 0 5 0 0 0 0 4 1-026 320 5 5 5 3 5 5 5 0 0 0 4 0 0 2 3 1-027 320 5 5 5 4 5 5 5 0 0 0 5 4 0 3 0 4 1-028 320 5 5 5 4 5 5 5 3 3 5 0 0 4 0 4 1-029 320 5 5 5 4 3 5 5 0 0 0 5 0 0 0 0 3 1-030 320 3 2 2 0 3 5 3 0 0 4 0 0 0 0 1-031 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 1-032 320 5 5 5 5 5 5 5 4 4 5 4 0 5 4 5 1-033 320 5 5 5 4 5 5 5 5 5 0 3 4 5 4 0 5 4 5 1-034 320 5 5 5 5 5 5 5 5 5 5 4 5 4 0 4 4 5 1-035 320 5 5 5 4 5 5 5 5 5 0 5 4 0 4 3 5 1-036 320 5 5 5 5 5 5 5 5 5 5 3 0 3 3 5 1-037 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1-038 320 5 5 5 0 5 5 5 4 3 0 0 0 0 5 3 1 3 0 4 1-039 320 5 5 5 4 5 5 5 5 5 5 4 0 4 3 4 1-040 320 4 4 5 3 4 4 5 0 0 0 5 0 0 0 0 3 1-041 320 5 5 5 5 5 5 5 3 3 0 3 5 4 1 4 4 1-042 320 5 5 5 3 5 5 5 5 4 0 0 5 3 0 1 0 4 1-043 320 5 5 5 4 5 5 5 4 4 0 5 4 1 4 4 5 1-044 320 5 5 5 2 5 5 5 5 4 5 4 0 2 4 1-045 320 0 0 0 0 0 4 0 0 0 0 0 0 0 0 0 0 1-046 320 5 4 5 5 5 5 5 4 2 0 5 4 0 4 0 4 1-047 320 3 0 3 0 0 3 0 0 0 0 0 0 0 4 0 0 0 0 1-048 320 5 5 5 1 5 5 5 3 1 0 0 0 0 5 3 0 2 0 0 1-049 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1-050 320 5 4 4 0 0 4 0 1 0 0 0 5 0 0 0 0 0 1-051 320 5 5 5 3 5 5 5 5 4 0 0 0 5 4 3 2 0 4 1-052 320 5 5 5 4 5 5 5 4 3 0 0 0 5 3 0 5 0 3 1-053 320 5 4 5 0 3 5 3 1 0 0 0 0 5 1 0 0 0 3 1-054 320 5 5 4 0 1 5 1 0 0 0 0 0 5 0 0 0 0 1 1-055 320 5 4 4 0 1 5 2 0 0 0 0 0 5 0 0 0 0 0 1-056 320 5 5 5 3 5 5 5 4 3 0 0 5 3 0 5 0 4 1-057 320 4 4 4 0 4 5 4 3 1 0 0 5 0 0 0 0 4 1-058 320 5 5 5 1 5 5 4 4 2 0 0 0 5 4 0 0 0 3 1-059 320 4 4 4 0 3 5 5 1 0 0 4 3 0 0 0 0 1-060 320 5 5 5 3 5 5 5 4 5 0 0 0 5 4 0 2 0 3 1-062 320 5 5 5 0 5 5 4 0 0 0 0 0 0 5 4 0 0 0 3 1-063 320 5 5 5 3 5 5 5 2 0 0 5 4 0 3 0 1-064 320 5 5 5 3 5 5 5 5 4 0 0 5 5 2 3 0 4 1-065 320 5 5 5 3 5 5 5 4 5 0 0 5 5 0 4 0 4 1-066 320 4 4 5 0 5 5 5 0 0 0 0 0 0 5 4 0 0 0 0 1-067 320 5 5 5 3 5 5 5 5 5 0 0 0 5 3 0 5 0 4 1-068 320 5 5 5 3 5 5 5 4 4 0 0 0 5 5 0 4 0 4 1-069 320 5 4 5 3 5 5 5 4 4 0 0 5 5 0 4 0 4 1-070 320 4 4 4 0 5 5 5 0 0 0 0 0 0 5 1 0 0 0 0 1-071 320 5 5 5 4 5 5 5 4 4 0 0 0 5 4 0 4 4 1-072 320 5 5 5 4 5 5 5 4 5 0 0 0 5 5 0 4 0 4 1-073 320 5 5 5 4 5 5 5 5 5 5 4 0 4 4 1-074 320 5 5 5 4 5 5 5 5 5 0 0 0 0 5 4 0 4 0 4 1-075 320 5 5 5 5 5 5 5 5 0 0 5 5 0 4 1-076 192 5 5 5 4 4 5 5 4 4 0 0 0 5 2 0 4 0 4 1-078 320 5 5 2 0 3 5 4 0 0 0 0 5 4 0 0 0 1 1-079 320 5 5 5 3 5 5 5 5 4 0 0 0 5 4 1 4 0 4 1-080 320 5 5 5 3 5 5 5 4 5 0 0 5 4 1 4 0 4 1-081 320 5 5 5 3 5 5 5 4 4 0 0 0 5 4 1 4 0 4 1-082 320 5 5 5 3 5 5 5 5 5 0 0 5 4 2 3 0 4 1-083 320 5 5 5 3 5 5 5 4 5 0 0 0 5 4 1 4 0 4 1-085 320 0 5 1 0 3 3 3 0 0 0 0 0 5 0 0 0 0 0 1-086 320 2 4 4 3 3 5 3 0 0 0 0 0 5 1 0 0 0 2 1-087 320 5 5 5 3 5 5 5 5 5 0 0 0 5 3 2 5 4 5 1-088 320 5 5 5 3 5 5 5 0 1 0 0 0 5 4 0 3 0 4 1-089 320 5 5 5 2 5 5 5 2 3 0 0 0 5 5 0 4 0 4 1-090 320 5 5 5 3 5 5 5 4 0 0 0 0 5 3 0 4 0 4 1-091 320 5 5 5 3 5 5 5 1 0 0 0 0 5 5 0 4 0 3 1-092 320 5 5 5 2 4 5 5 3 3 0 0 5 5 0 4 0 4 1-093 320 5 5 5 3 5 5 5 4 3 0 0 0 0 5 5 0 4 0 4 1-094 320 5 5 5 3 5 5 5 2 4 0 0 0 5 4 1 3 0 4 1-095 320 5 5 5 3 5 5 5 4 4 0 0 0 1 5 5 0 4 0 4 1-096 320 5 5 4 3 5 5 5 4 4 0 0 0 5 4 1 3 0 3 1-097 320 0 2 2 1 2 2 0 0 0 3 0 0 0 2 1 0 0 0 3 1-098 320 5 5 5 2 5 5 5 4 4 0 0 0 5 5 2 3 0 5 1-099 320 5 5 5 2 5 5 5 5 3 0 0 0 5 5 3 3 2 5 1-100 320 5 5 5 3 5 5 5 4 2 0 0 1 5 5 2 5 0 3 1-101 320 5 5 5 3 5 5 5 5 3 0 0 0 0 5 5 2 3 3 5 1-102 320 4 5 5 0 5 5 5 0 0 0 0 5 0 0 0 0 0 1-103 320 5 5 5 3 5 5 4 5 5 0 0 0 0 5 5 1 4 0 3 1-104 320 5 5 5 3 5 5 5 4 0 0 0 0 5 1 0 1 0 2 1-105 320 5 5 5 1 5 5 5 1 4 0 0 0 0 5 1 0 3 0 3 1-106 320 5 5 5 3 5 5 5 0 0 0 0 0 0 5 1 0 3 0 3 1-107 320 5 3 5 0 5 5 5 0 0 0 0 5 0 0 0 0 2 1-108 320 5 5 5 3 5 5 5 4 0 0 0 0 5 5 0 4 0 4 1-109 320 5 5 5 2 5 5 5 4 3 0 0 0 2 5 1 0 2 0 4 1-110 320 5 5 5 4 5 5 5 0 0 0 0 0 0 5 4 0 5 0 1 1-111 320 5 5 5 3 5 5 5 4 0 0 0 0 0 5 1 1 5 0 4 1-112 320 4 5 4 3 5 5 5 0 0 0 0 0 0 5 1 0 0 0 0 1-113 320 1 0 0 3 3 5 5 0 0 0 0 0 0 2 0 0 0 0 0 1-114 320 5 5 0 3 4 5 5 0 0 0 0 0 0 3 0 0 0 0 1 1-116 320 1 3 3 3 4 4 3 2 5 0 0 0 0 1 0 0 0 0 2 1-117 320 4 5 5 0 4 4 5 0 0 0 0 0 0 5 0 0 0 0 2 1-118 320 3 2 4 0 3 3 3 0 0 0 0 0 0 5 0 0 0 0 1 1-119 320 4 4 5 4 4 5 5 0 0 0 0 0 0 5 0 0 0 0 3 1-120 320 0 0 0 0 0 4 3 0 0 0 0 0 0 0 0 0 0 0 0 1-121 320 5 5 5 4 5 5 5 0 0 0 0 0 0 5 1 0 0 0 3 1-122 320 2 3 4 2 5 5 4 0 0 0 0 0 0 4 2 0 0 0 0 1-123 320 5 5 5 4 5 5 5 3 0 0 0 0 0 5 3 0 0 0 3 1-124 320 0 3 1 0 2 3 0 0 0 0 0 0 0 1 0 0 0 0 0 1-125 320 5 5 5 3 0 5 5 0 0 0 0 0 0 5 2 0 3 0 0 1-126 320 0 0 0 0 3 4 0 0 0 0 0 0 0 0 0 0 0 0 0 1-130 320 0 0 0 0 3 3 3 0 0 0 0 0 0 0 0 0 0 0 0 1-131 320 4 5 5 3 5 5 5 0 0 0 0 3 5 0 0 0 0 4 1-133 320 4 4 4 0 5 3 0 0 0 0 0 0 0 4 0 0 0 1-134 320 5 5 5 2 5 5 3 4 0 0 0 0 5 5 0 2 0 0 1-135 320 5 5 5 3 5 5 0 0 0 0 0 2 5 0 0 0 0 2 1-136 320 5 5 5 3 5 5 0 0 0 0 0 2 0 0 3 0 3 1-137 320 5 5 5 2 5 5 0 0 0 0 0 5 0 0 0 0 0 1-138 320 4 5 0 5 5 0 0 0 0 0 0 5 0 0 0 0 0 1-139 320 5 5 5 4 5 5 5 4 3 0 0 0 5 5 0 3 0 4 1-140 320 5 5 5 4 5 5 5 5 5 0 0 0 0 5 4 1 5 0 4 1-142 320 5 5 5 3 5 5 0 0 0 0 0 5 0 0 3 0 3 1-143 320 1 1 0 2 2 4 5 0 0 0 0 0 0 0 0 2 0 0 1-144 320 5 5 5 2 4 4 0 0 0 0 0 0 5 3 0 0 0 2 1-145 320 5 5 5 4 5 5 5 4 4 0 3 0 3 5 5 0 5 0 4 1-146 320 5 5 5 4 5 5 5 5 5 0 1 0 5 5 1 0 5 3 5 1-147 320 5 5 5 5 5 5 5 5 5 0 2 0 3 5 5 0 5 0 4 1-148 320 5 5 5 0 5 5 5 5 2 0 0 0 5 3 0 0 0 4 1-149 320 5 5 5 0 5 5 5 5 4 0 0 0 5 2 0 5 0 4 1-150 320 5 0 0 2 5 5 0 0 0 0 0 0 0 1 0 0 1-151 320 5 0 3 5 5 0 0 0 0 0 0 1 0 0 0 0 0 1-152 320 0 0 0 0 3 2 0 0 0 0 0 0 0 0 0 0 0 0 1-153 320 5 1 0 0 3 4 0 0 0 0 0 0 1 0 0 2 0 0 1-154 320 5 5 5 0 5 5 5 4 4 0 0 0 0 5 0 0 3 0 4 1-155 320 5 5 5 4 5 5 5 5 0 0 0 5 3 0 3 0 4 1-156 320 5 5 5 4 5 5 5 5 0 2 5 1 0 5 1 4 1-159 320 4 3 3 0 4 5 0 0 0 0 0 0 3 0 0 1 0 0 1-160 320 5 5 5 0 5 5 4 4 0 0 0 0 5 0 0 2 0 4 1-161 320 5 0 0 0 3 3 0 0 0 0 0 3 0 0 3 0 2 1-162 320 5 5 5 3 5 5 5 4 0 0 0 0 5 2 0 4 0 4 1-163 320 5 5 5 3 5 5 4 0 0 0 0 5 1 0 0 0 4 2-001 102 5 4 5 0 4 5 2 3 1 0 0 0 5 4 0 0 0 3 2-002 320 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 2-003 320 4 0 0 0 4 5 5 0 0 0 0 2 0 0 0 0 0 2-005 269 5 4 5 0 4 5 1 0 0 0 0 5 0 0 0 0 4 2-006 320 5 5 5 3 5 5 5 4 0 0 0 0 0 5 2 0 0 0 4 2-007 320 5 4 5 0 3 5 3 0 0 0 0 0 5 0 0 0 0 4 2-008 320 0 0 0 0 0 3 0 0 0 0 0 0 0 0 0 0 0 0 0 2-009 320 2 0 1 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 2-010 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2-011 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2-012 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2-013 320 1 1 1 0 0 1 0 0 0 0 0 0 0 5 0 0 0 0 0 2-014 320 5 5 5 0 2 4 2 0 0 0 0 0 5 3 0 0 0 0 2-015 320 3 3 1 0 2 5 3 0 0 0 0 4 0 0 0 0 0 2-016 320 5 5 5 0 4 5 2 0 0 5 3 0 0 2 2-017 320 5 5 5 0 3 5 3 4 0 0 0 0 5 0 0 0 0 5 2-018 320 5 5 5 0 3 5 2 4 3 0 0 5 2 0 0 0 3 2-020 320 5 5 4 0 0 4 0 0 1 0 5 3 0 0 0 0 2-021 320 5 5 4 0 5 5 0 1 2 0 0 0 5 4 0 0 0 1 2-022 320 0 4 0 0 0 4 0 0 0 0 0 0 4 0 0 0 0 0 2-024 320 5 5 4 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 2-025 320 4 5 4 0 0 4 0 0 0 0 0 0 0 5 0 0 0 0 0 2-026 320 5 5 5 0 3 5 2 0 0 0 0 5 1 0 0 0 4 2-027 320 3 5 3 0 1 2 0 0 0 0 0 4 1 0 0 0 0 2-028 320 4 5 1 0 3 5 2 1 0 0 0 0 0 5 2 0 0 0 0 2-030 320 4 5 1 0 3 4 4 0 0 0 0 0 0 5 1 0 0 0 0 2-031 320 5 5 5 0 3 5 2 1 0 0 0 0 5 5 0 3 0 3 2-032 320 4 5 4 0 5 5 0 0 0 0 0 0 5 1 0 0 0 1 3-001 320 2 0 0 0 1 4 5 0 0 0 0 0 0 2 0 0 0 0 0 3-002 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 4-001 320 2 0 0 0 3 5 5 0 0 0 5 0 0 0 0 1 5-001 320 4 0 1 0 2 5 5 0 0 0 5 0 0 0 0 5-002 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6-001 320 5 5 5 5 5 5 5 0 0 0 0 5 5 0 5 0 2 6-002 320 2 3 2 0 2 5 4 0 0 0 5 0 0 0 0 0 6-003 320 5 5 5 3 5 5 5 5 3 0 0 5 4 0 0 0 4 6-004 320 5 5 5 4 5 5 5 0 4 0 5 2 0 0 4 6-005 320 5 5 5 4 5 5 5 0 0 0 0 0 5 3 1 4 0 0 6-006 320 5 5 5 4 5 5 5 4 3 0 0 2 5 5 0 5 0 4 6-007 320 5 5 5 4 5 5 5 4 3 0 0 0 5 5 0 5 0 6-008 320 5 5 5 4 4 5 5 0 0 0 0 0 5 3 0 4 0 0 6-009 320 5 5 5 4 5 5 5 5 5 4 5 5 0 5 2 4 6-010 320 5 5 5 3 5 5 5 3 1 0 5 4 0 4 0 0 6-015 320 5 5 5 0 5 5 5 3 5 3 2 5 5 0 0 0 4 6-016 320 5 5 4 0 0 0 5 0 2 0 0 0 0 2 0 0 0 0 0 6-017 320 5 5 3 0 4 5 0 1 0 0 0 0 3 0 0 0 0 0 6-018 320 5 5 5 0 5 5 5 0 0 0 0 0 0 3 0 0 0 0 0 6-023 320 1 3 0 0 4 5 4 0 0 0 0 5 1 0 0 3 6-025 320 3 4 0 2 2 5 4 0 0 0 0 0 5 0 0 0 0 0 6-026 320 4 4 1 0 1 1 0 0 2 0 0 0 0 5 0 0 0 0 0 6-029 320 5 5 5 4 5 5 5 0 0 3 4 5 2 0 4 0 2 6-031 320 0 0 0 0 0 3 0 0 4 0 0 0 0 0 0 0 3 6-034 320 5 5 5 4 5 5 5 1 2 0 0 4 2 1 0 0 0 1 6-035 320 5 5 5 3 4 5 5 0 0 3 0 3 5 2 0 0 0 0 6-037 320 5 5 5 5 5 5 5 5 3 0 0 0 1 5 5 2 5 0 3 6-038 320 5 4 5 2 5 5 5 5 4 0 0 1 5 5 1 1 0 5 6-049 320 5 5 5 5 5 5 5 4 4 4 4 3 4 5 5 0 5 3 5 6-050 320 5 4 4 2 4 5 0 0 0 3 0 5 1 0 0 0 2 6-051 320 5 5 5 1 5 5 5 1 5 0 2 0 0 5 1 1 2 0 4 6-052 320 4 3 4 0 0 0 5 0 0 0 2 0 0 1 0 0 0 0 3 6-053 320 4 3 2 1 0 0 0 0 0 0 0 2 1 0 0 0 0 6-055 320 5 5 5 0 4 5 5 3 0 0 0 0 0 5 5 0 0 0 0 6-056 320 0 2 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 6-057 320 5 5 5 0 3 5 4 0 0 0 0 0 0 5 1 0 1 0 1 6-058 320 5 5 5 5 5 5 5 5 5 5 5 5 5 5 0 5 4 5 6-059 320 5 5 2 3 5 1 5 0 0 0 0 3 3 0 0 0 0 0 0 6-060 320 5 5 4 0 3 3 0 0 5 0 0 0 2 3 0 0 0 0 0 6-061 320 5 5 5 4 5 5 5 1 3 3 4 5 0 0 2 0 3 6-062 320 3 5 5 0 4 0 5 0 0 3 0 3 0 0 0 0 0 0 6-063 320 5 1 0 0 0 0 5 0 0 0 0 0 0 0 0 0 0 0 0 6-064 320 5 5 5 0 4 0 5 0 0 0 0 0 0 0 0 0 0 0 0 6-065 320 5 5 5 4 5 5 5 0 4 3 4 4 3 5 5 0 5 2 3 6-066 320 5 5 5 5 5 5 5 0 2 0 0 0 3 5 4 0 4 0 2 6-073 320 5 5 5 3 2 5 0 0 0 0 0 0 0 5 3 0 2 0 3 6-074 320 0 2 0 0 0 0 0 0 0 0 0 0 0 3 0 0 0 0 0 6-075 320 0 0 0 0 4 4 3 0 0 0 0 0 0 0 0 0 0 0 0 6-076 320 5 5 5 3 0 5 5 5 1 0 0 0 0 5 5 0 0 0 2 6-077 320 5 5 5 4 5 5 5 5 5 4 3 4 4 5 0 0 0 1 4 6-078 320 5 5 0 3 0 0 3 1 0 0 0 0 1 0 1 0 0 0 6-079 320 5 5 5 0 3 5 5 1 4 0 0 0 3 3 0 0 3 0 0 6-080 320 5 5 5 0 5 5 5 0 1 0 0 0 0 0 0 0 0 0 0 6-082 320 5 5 5 3 5 5 5 2 0 0 0 3 1 0 0 0 0 0 6-083 320 5 5 0 0 5 1 5 0 0 0 0 0 3 0 0 0 0 0 0 6-084 320 5 5 5 5 5 5 0 4 3 3 3 4 2 0 5 2 0 1 6-085 320 5 5 5 5 5 5 4 5 5 5 4 4 1 1 5 3 3 4 6-086 320 5 5 5 4 5 5 0 3 3 4 4 1 0 5 2 1 4 6-087 320 5 5 5 0 4 3 0 0 0 0 0 2 0 0 3 0 0 1 6-088 320 5 5 5 5 5 5 3 0 5 5 4 4 0 0 5 0 0 3 6-089 320 5 4 1 0 2 3 0 0 0 0 0 0 0 0 0 0 0 0 6-091 320 5 5 5 5 5 5 5 4 3 4 0 4 5 5 1 5 1 4 6-092 320 5 5 3 3 3 5 0 0 0 0 0 4 0 0 0 0 0 6-093 320 5 5 5 0 3 1 0 0 5 0 4 1 0 0 0 0 0 6-094 320 5 5 5 5 5 5 4 0 5 0 0 3 5 1 0 0 0 4 6-095 320 5 5 5 3 5 5 5 1 0 0 0 0 5 2 0 2 0 4 6-096 320 4 4 4 3 3 5 0 0 0 0 0 5 3 0 0 0 0 6-099 320 5 5 5 5 5 5 5 3 5 4 4 3 4 5 5 0 5 2 5 6-100 320 5 5 5 5 5 5 5 4 5 5 4 1 5 5 4 0 3 0 5 6-103 320 5 5 5 5 5 5 5 0 0 0 0 0 0 5 5 0 5 0 0 6-104 320 5 5 5 4 5 1 5 5 5 4 3 4 4 5 5 0 5 4 4 6-106 320 5 5 3 3 3 0 0 0 0 0 0 1 0 0 0 0 3 6-107 320 5 5 5 3 5 4 4 4 2 2 4 5 0 0 4 1 4 6-108 320 5 4 5 3 3 5 5 4 5 3 3 3 5 1 0 3 0 4 6-109 320 5 5 0 5 5 0 0 0 0 0 0 1 0 0 0 0 0 6-110 320 0 0 5 0 3 3 0 0 0 0 0 0 0 0 0 0 0 0 6-111 320 4 0 4 0 5 5 0 0 0 0 0 0 1 0 0 0 0 0 6-112 320 5 5 5 4 5 5 1 1 0 0 0 0 5 4 0 3 0 0 6-113 320 5 5 5 0 5 5 0 0 0 0 0 5 1 0 0 0 1 7-001 320 5 4 4 3 0 5 0 0 0 0 4 0 0 0 0 0 7-002 320 5 4 5 0 3 5 5 0 0 0 0 0 5 0 0 0 0 0 7-003 320 5 5 5 4 5 5 5 0 0 0 0 0 0 5 0 0 0 0 0 7-004 320 5 5 5 0 5 5 5 3 2 0 0 0 5 4 0 0 0 3 7-005 320 5 0 0 0 0 2 0 0 0 0 0 0 0 1 0 0 0 0 0 7-006 320 0 0 0 0 0 2 0 0 0 0 0 0 3 0 1 0 0 0 7-007 320 4 4 5 0 5 5 5 0 0 0 0 0 0 4 3 0 0 0 0 7-008 320 5 5 5 3 5 5 5 0 0 0 0 0 5 4 0 1 0 0 7-010 320 5 5 5 2 5 5 5 4 0 0 0 3 5 5 2 4 0 3 7-011 320 5 0 4 0 3 4 3 0 0 0 0 0 5 3 0 0 0 4 7-012 320 5 5 5 0 2 2 0 0 0 0 0 0 0 5 0 0 0 0 0 7-013 320 3 0 0 0 0 0 0 0 0 0 0 0 0 4 0 0 0 0 0 7-014 320 3 2 0 0 0 3 0 0 0 0 0 0 4 0 0 0 0 0 7-015 320 5 5 5 3 5 5 4 0 0 0 0 0 5 5 0 4 0 2 7-016 320 3 2 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7-017 320 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7-018 320 3 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7-019 320 3 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7-020 320 3 2 0 0 3 3 0 0 0 0 0 0 0 5 0 0 0 0 0 7-024 320 4 0 0 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 0 7-027 320 5 5 5 0 5 5 5 0 0 0 0 0 0 5 3 0 2 0 0 7-029 320 0 4 2 0 1 3 0 0 0 0 0 0 1 0 0 0 0 0 8-001 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 8-002 320 3 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 8-003 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 9-001 320 4 4 5 0 3 5 4 0 1 0 0 4 0 0 0 0 0 9-002 320 5 5 5 3 5 5 5 0 0 0 0 0 5 3 0 0 0 0 9-003 320 5 5 5 3 5 5 5 0 0 0 0 0 0 5 5 0 4 0 5 9-004 320 5 5 5 2 5 4 5 0 0 0 0 0 0 0 0 0 0 0 0 9-005 320 1 0 0 0 1 4 4 0 0 0 0 1 0 0 0 0 0 9-006 320 5 5 5 4 5 5 5 0 2 0 0 0 4 5 5 0 5 0 3 9-007 320 5 5 3 3 5 5 5 0 0 0 0 0 0 5 0 0 0 0 0 9-008 320 5 5 5 3 5 5 5 4 4 0 0 0 3 5 4 0 5 0 4 9-009 320 5 4 0 0 4 5 4 0 0 0 1 0 0 0 0 0 0 9-010 320 5 5 5 4 5 5 5 0 0 0 0 0 5 1 0 0 0 0 9-011 320 5 5 5 3 5 5 5 3 0 0 0 0 5 5 0 4 0 4 9-012 320 5 5 5 0 5 5 5 0 0 0 0 2 5 2 0 0 0 0 9-013 320 5 5 5 5 5 5 5 3 1 0 4 5 5 0 4 5 4 9-014 320 4 3 1 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 9-015 320 5 5 5 1 5 5 5 0 0 0 0 0 5 0 0 3 0 0 9-016 320 5 5 5 2 5 5 4 0 0 0 0 5 3 0 0 0 0 9-017 320 4 0 0 0 0 0 0 0 0 0 4 0 0 0 0 0 9-019 320 0 5 0 0 5 3 0 0 0 0 0 5 0 0 0 0 0 9-020 320 4 5 0 0 3 5 4 3 0 0 3 0 0 0 0 0 9-021 320 5 5 5 1 5 5 5 1 0 0 0 0 3 5 3 0 3 0 2 9-022 320 5 5 5 0 0 0 0 0 0 0 0 0 4 1 0 0 0 0 9-023 320 5 5 5 2 3 3 5 0 5 0 0 0 0 5 3 0 3 0 4 9-024 320 5 5 5 3 5 5 5 0 3 0 4 0 4 5 0 0 2 0 0 9-025 320 2 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 9-027 320 5 5 5 4 5 5 5 0 3 3 3 0 3 5 0 0 2 0 1 9-028 320 5 5 5 3 5 5 5 0 0 0 0 0 0 3 1 0 3 0 4 9-029 320 3 4 3 0 3 4 0 0 0 0 0 0 1 0 0 0 0 0 10-002  320 4 4 4 3 0 4 3 0 0 0 0 0 4 0 0 0 0 0 10-003  320 0 4 5 0 3 4 3 0 0 0 0 0 0 4 0 0 0 0 0 10-004  320 5 5 5 3 5 5 5 0 0 0 0 0 5 5 0 0 0 0 11-002  320 0 1 3 3 3 5 4 0 0 0 0 0 0 4 1 0 0 0 2 12-002  320 4 5 5 4 4 5 3 0 0 0 0 0 0 4 3 0 0 0 1 13-001  320 5 5 2 4 5 5 0 0 0 0 0 0 5 5 0 0 0 0 13-002  320 5 5 5 4 4 5 0 0 0 0 0 5 5 1 3 0 1 13-003  320 5 5 5 1 5 5 4 0 0 0 0 0 5 5 0 0 0 3 13-004  320 5 5 5 3 5 5 5 0 4 0 1 0 3 5 5 1 5 0 4 13-005  320 4 0 1 0 4 5 0 0 0 0 0 0 1 0 0 1 0 0 13-006  320 5 5 5 0 5 5 5 0 0 0 0 5 1 0 4 0 3 14-001  320 5 5 5 5 5 5 5 0 0 0 0 0 0 5 5 0 0 0 0 14-002  320 5 5 5 0 4 5 5 0 0 0 0 0 0 5 1 0 3 0 0

TABLE 26 Application herbicide amount No. (g/ha) F G H I J K L M N O P Q R b c d e f g 1-001 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1-002 320 5 5 5 5 5 5 5 4 5 4 4 4 4 5 5 4 5 5 5 1-003 320 5 5 5 5 5 5 5 4 3 3 2 3 3 5 5 3 5 3 4 1-004 320 5 5 5 5 5 5 5 4 4 3 3 4 5 5 4 5 3 4 1-005 320 5 5 5 5 5 5 5 4 4 3 4 4 3 5 5 4 5 3 4 1-006 320 5 5 5 5 5 5 5 4 3 0 0 0 2 5 3 4 3 0 3 1-007 320 0 0 0 3 3 5 1 0 0 0 0 0 0 0 0 0 0 0 0 1-008 320 5 5 4 4 5 5 4 2 0 0 0 0 0 4 0 2 0 0 3 1-009 320 0 0 0 0 1 4 0 1 0 0 0 0 0 0 0 0 0 0 0 1-010 320 5 5 5 5 5 5 5 4 4 4 4 4 4 5 5 4 5 4 4 1-011 320 3 0 0 0 4 5 5 0 0 0 0 2 0 0 0 0 4 1-012 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1-013 320 0 0 0 0 4 5 4 0 0 0 0 0 2 0 0 0 0 4 1-014 320 5 5 5 5 5 5 5 5 5 3 3 5 5 5 5 3 4 1-015 320 5 5 5 5 5 5 5 4 4 3 4 4 4 5 5 5 5 3 4 1-016 320 5 5 5 5 5 5 5 4 4 2 4 5 4 4 5 3 4 1-017 320 5 5 5 5 5 5 5 4 4 2 3 5 4 4 5 2 4 1-018 320 5 5 5 5 5 5 5 3 0 4 4 4 5 5 3 5 4 4 1-019 320 5 5 5 5 5 5 5 4 2 4 4 4 5 5 3 5 4 4 1-020 320 5 5 5 4 5 5 5 3 4 4 5 1 0 5 3 4 1-021 320 1 1 3 0 3 4 4 0 0 0 0 3 0 0 0 0 2 1-022 320 5 5 5 5 5 5 5 1 1 3 3 4 3 5 3 3 5 0 4 1-023 320 2 1 4 1 4 4 4 0 0 0 0 2 0 4 1 0 0 0 2 1-024 320 5 5 5 5 5 5 5 1 0 1 3 3 5 5 2 5 0 4 1-025 320 5 4 4 5 5 5 5 1 0 4 4 4 3 4 3 3 4 0 4 1-026 320 5 5 4 1 5 5 5 0 0 3 1 5 3 0 2 4 1-027 320 5 5 5 5 5 5 5 2 0 1 1 3 5 5 3 4 0 4 1-028 320 5 5 5 4 5 5 5 3 0 3 3 3 5 4 2 3 0 4 1-029 320 5 5 5 5 5 5 5 1 0 3 3 3 1 5 3 1 5 0 4 1-030 320 4 5 4 3 4 5 4 0 0 0 0 0 0 5 1 0 0 0 3 1-031 320 1 1 1 3 3 4 0 0 0 0 0 0 3 0 0 0 0 3 1-032 320 5 5 5 5 5 5 5 4 3 3 4 4 5 5 4 5 3 4 1-033 320 5 5 5 5 5 5 5 4 4 3 1 2 5 4 4 5 3 4 1-034 320 5 5 5 5 5 5 5 4 3 5 5 4 4 5 4 5 1-035 320 5 5 5 5 5 5 5 4 3 5 4 4 5 2 4 1-036 320 5 5 5 5 5 5 5 4 4 2 0 5 4 4 5 3 4 1-037 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1-038 320 5 5 5 5 5 5 5 4 2 0 0 0 1 5 4 4 4 1 4 1-039 320 5 5 5 5 5 5 5 4 4 3 5 4 4 5 3 4 1-040 320 4 4 5 4 5 5 5 1 0 0 0 0 5 3 0 0 0 4 1-041 320 5 5 5 5 5 5 5 4 3 3 3 3 3 5 5 4 5 1 4 1-042 320 5 5 5 5 5 5 5 3 0 0 0 0 1 5 4 3 5 1 4 1-043 320 5 5 5 5 5 5 5 4 3 2 4 3 2 5 5 4 5 3 4 1-044 320 5 5 5 5 5 5 5 4 2 0 0 0 5 4 4 5 2 4 1-045 320 4 5 5 5 5 5 5 0 0 0 0 0 0 5 3 1 0 0 2 1-046 320 4 5 5 5 5 5 5 3 2 2 2 0 4 5 5 3 4 0 4 1-047 320 1 1 3 0 3 4 1 0 0 0 0 0 0 4 0 0 0 0 3 1-048 320 4 4 5 4 5 5 5 3 1 3 3 1 3 5 4 0 0 1 3 1-049 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1-050 320 3 5 5 3 4 5 3 3 0 0 0 0 0 5 0 0 0 0 4 1-051 320 5 5 5 5 5 5 5 4 1 0 3 0 5 5 4 5 0 4 1-052 320 5 5 5 5 5 5 5 3 0 1 0 3 5 4 4 5 0 4 1-053 320 3 3 4 2 4 5 3 0 0 1 0 2 5 3 3 0 0 4 1-054 320 2 3 4 3 4 5 3 0 0 0 0 0 0 4 0 0 0 0 3 1-055 320 3 3 4 4 4 5 5 0 0 1 0 5 3 2 0 0 3 1-056 320 5 5 5 5 5 5 5 4 2 1 0 5 4 4 5 0 4 1-057 320 3 3 4 2 3 5 1 1 0 0 0 0 3 0 3 0 1 4 1-058 320 5 5 5 5 5 5 5 4 1 0 0 5 4 3 5 0 4 1-059 320 1 4 4 4 4 5 4 0 0 0 0 0 4 4 0 0 0 3 1-060 320 5 5 5 5 5 5 5 3 0 3 3 3 5 4 4 5 0 4 1-062 320 1 4 4 4 5 5 5 0 0 0 0 0 0 5 4 0 0 0 3 1-063 320 1 5 5 5 5 5 5 2 0 0 0 4 5 5 3 4 0 4 1-064 320 5 5 5 5 5 5 5 4 2 0 1 3 5 5 4 5 1 4 1-065 320 5 5 5 5 5 5 5 4 2 2 0 3 5 5 4 5 0 4 1-066 320 4 5 5 4 5 5 4 1 0 1 0 3 5 4 0 0 0 3 1-067 320 5 5 5 5 5 5 5 5 4 2 3 2 3 5 5 4 5 1 4 1-068 320 5 5 5 5 5 5 5 5 4 1 3 3 5 5 4 5 3 4 1-069 320 5 5 5 5 5 5 5 5 5 2 3 3 5 5 4 5 1 4 1-070 320 1 5 3 5 5 5 4 0 0 1 0 2 2 5 4 0 0 0 3 1-071 320 5 5 5 5 5 5 5 4 0 1 0 2 1 5 5 4 5 0 4 1-072 320 5 5 5 5 5 5 5 5 5 1 2 2 3 5 5 2 5 1 4 1-073 320 5 5 5 5 5 5 5 4 2 2 3 5 4 3 5 1 4 1-074 320 5 5 5 5 5 5 5 3 0 2 1 1 5 5 4 5 0 4 1-075 320 5 5 5 5 5 5 5 4 4 1 0 0 5 4 1 5 1-076 192 5 5 5 5 5 5 5 4 0 3 3 5 4 4 5 0 4 1-078 320 1 5 5 1 4 5 3 0 0 0 0 0 5 3 0 0 0 3 1-079 320 5 5 5 5 5 5 5 4 0 0 1 3 5 5 4 4 0 5 1-080 320 5 5 5 5 5 5 5 4 0 3 0 1 5 5 4 4 0 4 1-081 320 5 5 5 5 5 5 5 4 5 3 0 0 0 5 5 5 4 0 5 1-082 320 5 5 5 5 5 5 5 4 0 1 0 0 0 5 5 4 5 0 4 1-083 320 5 5 5 5 5 5 5 4 4 0 4 0 0 5 5 4 5 0 4 1-085 320 3 5 5 3 3 3 3 0 0 0 0 0 0 4 5 0 3 0 1 1-086 320 0 3 5 4 4 5 4 0 0 0 0 0 2 4 3 0 0 0 3 1-087 320 5 5 5 5 5 5 5 5 4 0 3 4 3 5 5 3 5 4 4 1-088 320 5 5 5 5 5 5 5 4 1 2 3 0 3 5 5 3 5 0 4 1-089 320 5 5 5 5 5 5 5 4 2 1 0 0 3 5 5 2 5 0 4 1-090 320 5 5 5 5 5 5 5 4 1 2 3 0 3 5 5 3 5 0 4 1-091 320 5 5 5 5 5 5 5 4 3 0 0 1 5 5 1 5 0 4 1-092 320 5 5 5 2 4 5 5 3 3 0 0 0 5 5 0 4 0 4 1-093 320 5 5 5 5 5 5 5 4 4 0 2 0 3 5 5 3 5 0 4 1-094 320 5 5 5 5 5 5 5 4 2 0 3 0 3 5 5 2 5 0 4 1-095 320 5 5 5 5 5 5 5 4 3 0 2 3 5 5 2 5 0 4 1-096 320 5 5 5 5 5 5 5 4 2 2 2 3 5 5 3 5 0 4 1-097 320 5 5 5 3 5 5 4 3 1 0 3 5 5 3 2 3 1-098 320 5 5 5 5 5 5 5 4 0 0 3 0 3 5 5 3 5 1 5 1-099 320 5 5 5 5 5 5 5 4 0 3 3 3 3 5 5 4 5 1 5 1-100 320 5 5 5 5 5 5 5 4 0 1 0 3 5 5 3 5 0 5 1-101 320 5 5 5 5 5 5 5 5 5 3 3 0 3 5 5 3 5 0 5 1-102 320 5 5 5 5 5 5 5 0 0 3 0 0 2 5 5 0 4 0 2 1-103 320 5 5 5 5 5 5 5 4 0 2 2 3 5 5 3 5 0 4 1-104 320 5 5 5 5 5 5 5 3 0 2 1 1 5 4 1 0 0 4 1-105 320 5 5 5 5 5 5 5 1 0 2 1 2 3 5 4 1 5 0 4 1-106 320 5 5 5 5 5 5 5 1 5 2 2 0 1 5 5 0 4 0 3 1-307 320 4 5 5 5 5 5 5 1 0 0 0 0 5 2 3 2 0 4 1-108 320 5 5 5 5 5 5 5 4 5 0 3 1 5 5 3 3 1 4 1-109 320 5 5 5 5 5 5 5 3 0 3 3 3 5 5 0 5 0 4 1-110 320 5 5 5 5 5 5 5 0 0 2 3 3 3 5 5 0 5 0 5 1-111 320 5 5 5 5 5 5 5 1 0 1 3 2 1 5 5 3 5 0 5 1-112 320 5 4 5 5 5 5 5 1 0 3 1 3 3 5 4 0 5 0 4 1-113 320 5 4 4 4 4 5 5 1 0 2 3 0 4 4 0 0 3 0 5 1-114 320 5 5 5 5 4 5 5 1 1 3 3 0 2 5 1 0 4 0 4 1-115 320 2 1 1 2 3 3 4 0 0 0 1 0 1 1 0 0 0 0 5 1-116 320 5 5 5 4 5 5 5 1 0 3 2 1 3 4 5 3 3 0 5 1-117 320 5 5 5 5 5 5 5 1 1 0 3 0 3 5 3 0 5 0 5 1-118 320 0 0 2 3 4 5 3 0 0 3 3 3 3 4 4 0 0 0 4 1-119 320 5 5 5 5 5 5 5 1 0 3 1 0 3 5 2 0 4 0 5 1-120 320 3 4 5 4 3 5 3 0 0 4 4 5 3 1 1 2 0 0 5 1-121 320 5 5 5 5 5 5 5 3 0 3 2 0 3 5 5 2 3 0 5 1-122 320 4 5 5 5 5 5 5 4 1 0 1 0 0 5 5 4 4 0 5 1-123 320 5 5 5 5 5 5 5 4 0 0 3 0 4 5 5 2 5 0 5 1-124 320 0 2 5 2 3 4 3 0 0 3 2 0 0 3 4 0 3 0 4 1-125 320 5 5 5 5 5 5 5 0 0 1 2 3 2 5 3 0 5 0 3 1-126 320 3 4 4 3 5 5 3 0 0 0 0 0 4 0 0 0 0 4 1-127 320 0 0 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 1-130 320 4 5 5 5 5 5 5 0 0 0 0 0 5 1 1 2 0 5 1-131 320 0 5 4 4 5 5 5 0 0 0 0 0 4 4 3 0 2 0 5 1-132 320 0 0 0 1 2 3 1 0 0 0 0 0 0 1 0 0 0 0 3 1-133 320 0 4 4 3 4 5 2 0 0 0 3 0 3 1 0 3 0 3 4 1-134 320 5 5 5 5 5 5 5 2 1 4 2 4 1 5 5 2 5 0 4 1-135 320 5 5 5 5 5 5 5 3 0 5 1 0 3 5 4 1 2 0 4 1-136 320 5 5 5 4 5 5 5 3 0 1 4 2 5 3 1 3 0 4 1-137 320 5 5 5 5 5 5 5 4 3 0 0 2 5 3 0 3 0 4 1-138 320 5 5 5 5 5 5 5 3 0 0 1 3 3 5 2 0 3 0 4 1-139 320 5 5 5 5 5 5 5 2 0 1 3 3 2 5 5 1 5 0 4 1-140 320 5 5 5 5 5 5 5 4 3 2 3 2 3 5 4 3 5 3 5 1-142 320 5 5 5 5 5 5 5 4 0 2 3 3 3 5 5 3 4 3 4 1-143 320 5 5 5 5 5 5 5 1 1 0 0 0 0 2 3 1 3 0 4 1-144 320 5 5 5 5 5 5 5 4 1 0 2 2 3 5 5 3 4 2 4 1-145 320 5 5 5 5 5 5 5 3 0 1 2 2 3 5 5 2 5 2 4 1-146 320 5 5 5 5 5 5 5 5 0 2 3 3 3 5 5 4 5 4 5 1-147 320 5 5 5 5 5 5 5 4 1 1 3 4 4 5 5 3 5 3 4 1-148 320 5 5 5 5 5 5 5 4 2 1 3 3 3 5 4 3 5 3 5 1-149 320 5 5 5 5 5 5 5 4 0 2 3 3 2 5 4 2 5 2 4 1-150 320 5 4 5 5 5 5 5 3 0 0 0 0 0 5 4 0 4 0 4 1-151 320 5 5 5 5 5 5 5 3 0 0 0 0 1 4 4 2 3 2 4 1-152 320 5 5 5 4 5 5 5 4 3 0 0 0 0 5 2 1 3 0 4 1-153 320 5 5 5 5 5 5 5 4 4 0 0 3 0 5 3 1 5 0 4 1-154 320 5 5 5 5 5 5 5 4 3 1 2 3 3 5 3 3 5 1 4 1-155 320 5 5 5 5 5 5 5 4 2 0 2 0 3 5 4 3 5 2 4 1-156 320 5 5 5 5 5 5 5 4 3 2 3 3 4 5 4 3 5 3 4 1-158 320 0 0 1 3 1 4 0 0 0 0 0 0 0 1 0 0 0 0 2 1-159 320 5 1 4 5 5 5 5 4 3 0 0 0 0 3 0 1 2 2 4 1-160 320 5 5 5 5 5 5 5 4 0 2 3 4 3 5 4 2 5 5 5 1-161 320 4 0 4 4 5 5 5 0 0 0 0 0 0 3 1 0 2 0 3 1-162 320 5 5 5 5 5 5 5 4 1 4 4 4 3 5 4 2 5 3 4 1-163 320 5 5 5 5 5 5 5 4 3 3 3 3 3 5 4 2 5 4 5 1-166 320 1 1 4 5 4 5 5 3 0 0 0 0 0 3 1 1 1 0 4 2-001 102 5 4 5 4 5 5 4 1 2 3 3 3 2 4 3 0 0 1 4 2-002 320 4 4 3 1 4 5 2 0 0 3 2 2 1 4 0 0 0 0 3 2-003 320 4 5 5 5 5 5 4 1 0 0 0 0 3 5 3 0 0 0 3 2-005 269 3 4 5 3 5 5 3 0 0 0 0 0 0 5 3 0 0 2 4 2-006 320 3 3 4 3 4 5 3 0 0 0 0 0 0 4 0 0 0 0 0 2-007 320 1 0 1 0 4 4 3 0 0 0 2 0 3 1 0 0 0 1 2-008 320 2 3 3 0 3 4 0 0 1 0 0 0 4 1 1 0 0 3 2-009 320 0 0 3 0 1 1 0 0 0 0 0 0 0 4 0 0 0 0 0 2-010 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2-011 320 0 0 2 0 1 2 0 0 0 0 0 0 0 3 0 0 0 0 0 2-012 320 0 0 1 0 1 3 0 0 0 0 0 0 0 4 0 0 0 0 0 2-013 320 4 5 5 3 5 5 4 0 0 1 1 1 2 5 4 0 0 0 4 2-014 320 3 5 5 4 5 5 4 3 0 0 0 0 3 5 3 0 0 0 4 2-015 320 5 5 5 4 5 5 3 1 0 0 0 0 0 5 4 1 0 0 4 2-016 320 5 5 5 4 5 5 4 4 3 0 0 0 0 5 4 3 0 0 4 2-017 320 5 5 5 4 4 5 3 1 0 0 0 5 2 0 0 0 4 2-018 320 1 1 1 0 1 4 1 0 0 0 0 2 0 0 0 0 0 2-020 320 3 5 4 0 4 5 0 0 0 0 0 0 4 1 0 0 0 0 2-021 320 4 4 4 3 5 5 0 0 0 0 0 0 0 4 3 0 0 0 3 2-022 320 0 0 1 0 3 5 2 0 0 0 0 0 5 3 0 0 0 1 2-023 320 0 0 1 0 0 1 0 0 0 0 0 0 3 0 0 0 0 0 2-024 320 4 5 5 2 4 5 2 0 0 0 0 2 5 3 0 0 0 3 2-025 320 4 5 4 0 4 5 3 0 0 0 0 0 0 4 1 0 0 0 3 2-026 320 4 5 4 4 4 5 3 0 0 0 0 0 0 5 2 0 0 0 3 2-027 320 0 5 3 1 2 4 0 0 0 0 0 0 4 1 0 0 0 1 2-028 320 2 5 5 0 4 5 1 0 0 0 0 0 0 5 4 0 0 0 3 2-029 320 0 0 0 2 0 1 0 0 0 0 0 0 0 2 0 0 0 0 0 2-030 320 4 5 4 1 3 5 2 0 0 0 0 0 1 5 2 0 0 0 3 2-031 320 5 5 5 5 5 5 4 0 0 0 0 0 4 5 5 0 0 0 4 2-032 320 2 5 5 3 4 5 5 0 0 0 0 0 0 5 1 0 1 0 4 3-001 320 4 3 4 2 3 4 3 0 0 0 0 0 4 2 0 0 0 0 3-002 320 0 2 1 0 0 1 0 0 0 0 0 0 0 3 0 0 0 0 0 4-001 320 3 1 2 4 5 5 2 0 0 0 0 4 1 0 0 0 5-001 320 4 3 3 4 5 5 4 0 0 0 0 0 4 2 0 0 0 5-002 320 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6-001 320 5 5 5 5 5 5 5 0 0 0 0 0 5 5 0 5 0 2 6-002 320 5 5 5 5 5 5 5 1 0 0 0 0 5 5 0 0 0 0 6-003 320 5 5 5 5 5 5 5 3 0 1 2 3 0 5 5 3 0 0 4 6-004 320 5 5 5 4 5 5 5 3 2 3 3 3 5 4 1 0 4 6-005 320 5 5 5 5 5 5 5 5 4 3 3 5 5 4 4 0 0 6-006 320 3 3 4 1 5 4 3 0 0 0 0 4 1 0 5 4 6-007 320 5 5 5 3 5 5 4 1 0 0 0 5 5 2 5 0 6-008 320 0 5 5 0 5 3 3 0 0 0 0 0 3 3 1 4 0 0 6-009 320 5 5 5 4 5 5 5 3 0 2 0 5 5 3 5 2 4 6-010 320 5 5 5 3 5 4 5 0 0 3 0 0 5 4 3 4 0 0 6-015 320 5 5 5 4 5 5 5 2 2 4 3 2 5 5 3 0 0 4 6-016 320 5 5 5 4 4 5 5 0 0 3 0 3 5 5 0 0 0 1 6-017 320 5 5 5 5 5 5 5 0 0 4 1 0 3 5 5 0 1 0 3 6-018 320 5 5 5 4 5 5 5 0 0 3 3 4 5 5 3 2 1 3 6-023 320 5 5 5 5 5 5 4 0 0 0 0 1 5 3 0 3 3 6-024 320 0 3 1 1 3 5 1 0 0 0 0 0 0 0 0 0 0 0 3 6-025 320 4 5 5 5 5 5 5 0 0 0 0 0 0 5 4 0 1 0 3 6-026 320 5 5 5 5 5 5 3 0 0 0 0 0 1 5 5 0 3 0 3 6-027 320 3 4 4 1 0 0 0 0 0 0 0 0 0 1 1 0 0 0 0 6-029 320 5 5 5 5 5 5 5 4 5 4 3 5 4 5 5 0 5 0 4 6-030 320 4 4 1 0 1 1 0 0 0 0 0 0 0 1 0 0 0 0 3 6-031 320 5 5 5 5 5 5 4 2 0 3 0 1 5 4 0 0 0 3 6-032 320 4 3 4 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6-033 320 0 0 1 3 0 5 0 0 0 0 0 0 3 3 0 0 0 1 6-034 320 5 5 5 5 5 4 5 3 3 3 3 5 3 5 5 0 0 0 4 6-035 320 5 5 5 5 5 5 5 4 5 3 3 4 4 5 5 2 4 0 4 6-036 320 4 4 5 3 3 5 3 0 0 0 1 0 3 4 4 0 0 0 3 6-037 320 5 5 5 5 5 5 5 5 5 3 4 3 5 5 4 5 3 5 6-038 320 5 5 5 5 5 5 5 5 5 3 4 0 3 5 5 4 3 0 5 6-049 320 5 5 5 0 5 5 5 3 4 5 5 5 5 5 5 2 5 4 5 6-050 320 4 2 4 3 5 5 4 0 0 3 3 3 3 5 4 0 0 2 5 6-061 320 5 5 5 4 5 5 5 1 3 5 4 4 4 5 5 1 4 3 5 6-052 320 5 5 5 2 4 5 4 0 0 0 0 0 0 5 3 0 0 0 3 6-053 320 5 5 5 3 3 5 4 0 0 0 0 0 0 3 2 0 0 0 3 6-054 320 4 5 5 3 5 4 5 0 0 4 0 0 0 3 4 0 0 0 1 6-055 320 5 5 5 5 5 5 5 1 0 3 4 3 4 5 5 3 3 0 5 6-056 320 5 5 4 3 3 4 3 0 0 3 0 0 2 1 0 0 0 3 6-057 320 5 5 5 5 5 5 5 1 1 4 4 3 4 5 5 3 5 0 5 6-058 320 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 2 5 5 5 6-059 320 5 5 5 5 5 5 5 5 5 5 4 4 5 5 5 0 5 0 5 6-060 320 5 4 5 5 5 5 5 5 4 4 4 4 4 5 5 1 4 2 5 6-061 320 5 5 5 5 5 5 5 4 1 4 3 3 4 5 5 3 5 3 4 6-062 320 5 5 5 5 5 4 5 3 1 3 5 5 5 5 0 5 0 4 6-063 320 5 5 5 5 3 5 5 2 0 0 3 0 3 5 0 4 0 4 6-064 320 5 5 5 5 3 5 5 4 0 4 5 5 0 5 0 3 6-065 320 5 5 5 5 5 5 5 2 0 1 3 3 3 5 5 1 5 3 4 6-066 320 5 5 5 5 5 5 5 3 3 4 3 4 4 5 5 3 5 0 4 6-068 320 0 3 3 0 0 0 0 0 0 0 2 0 0 1 4 0 0 0 2 6-071 320 0 0 0 0 3 4 2 0 0 0 0 0 0 1 0 0 2 0 0 8-072 320 0 4 1 3 0 2 0 0 0 0 0 0 0 2 3 0 0 0 0 6-073 320 5 5 5 5 5 5 3 0 0 3 2 3 3 5 4 0 3 0 4 6-074 320 0 4 3 1 0 2 0 0 0 0 0 0 0 2 0 0 0 0 0 6-075 320 1 0 2 5 5 5 5 0 0 0 0 0 0 4 4 0 2 0 3 6-076 320 5 5 5 5 5 5 5 5 1 2 2 3 2 5 5 1 5 0 4 6-077 320 5 5 5 5 5 5 5 5 1 4 4 4 4 5 5 2 5 4 5 6-078 320 5 5 5 5 5 4 5 4 0 1 3 3 5 0 5 0 4 6-079 320 5 5 5 5 5 5 5 4 0 3 3 4 3 5 5 1 5 0 4 6-080 320 5 5 5 5 5 5 5 4 0 0 0 4 4 5 5 1 5 0 3 6-081 320 4 0 4 5 3 4 5 0 0 0 0 0 0 0 5 0 3 0 3 6-082 320 5 5 5 5 5 5 5 4 1 1 4 4 5 5 0 5 0 4 6-083 320 5 5 5 5 5 4 5 5 3 5 1 4 5 5 0 4 3 4 6-084 320 5 5 5 5 5 5 5 3 3 4 3 3 4 5 0 5 4 0 4 6-085 320 5 5 5 5 5 5 5 4 3 5 3 4 4 5 3 5 5 4 5 6-086 320 5 5 5 5 5 5 5 3 0 5 4 5 5 3 5 5 3 4 6-087 320 5 5 5 0 4 4 3 0 0 0 1 4 1 0 3 1 0 4 6-088 320 5 5 5 5 5 5 5 3 0 5 4 4 5 5 2 5 4 0 4 6-089 320 5 5 4 5 4 4 3 4 4 0 4 6-090 320 5 5 4 4 3 4 2 0 0 0 0 0 0 1 2 0 0 0 4 6-091 320 5 5 5 5 5 5 5 4 2 3 4 3 4 5 5 4 5 3 5 6-092 320 5 5 4 5 5 5 3 0 0 5 3 4 4 4 2 1 0 0 4 6-093 320 5 5 5 5 5 5 5 3 3 5 4 5 5 4 5 2 5 3 4 6-094 320 5 5 5 5 5 5 5 4 0 5 3 5 4 5 5 4 4 4 6-095 320 5 5 5 5 5 5 5 4 0 5 1 0 3 5 5 3 4 0 4 6-096 320 5 4 5 3 1 1 0 3 3 0 4 6-098 320 3 3 2 1 3 5 4 0 0 0 0 0 0 2 1 0 2 0 0 6-099 320 5 5 5 5 5 5 5 3 4 5 4 5 5 5 5 4 5 4 5 6-100 320 5 5 5 5 5 5 5 3 4 4 3 4 3 5 5 3 5 0 5 8-103 320 5 5 5 5 5 5 5 2 0 0 1 0 2 5 5 0 5 0 4 6-104 320 5 5 5 5 5 5 5 5 5 4 4 4 4 5 5 3 5 4 4 6-105 320 5 5 5 2 2 4 2 0 0 0 0 3 3 3 3 0 0 0 4 6-106 320 5 5 5 3 5 5 5 0 0 0 3 3 3 3 5 1 3 0 5 6-107 320 5 5 5 5 5 5 5 3 2 4 2 5 4 5 5 1 5 2 4 6-108 320 5 5 5 5 5 5 5 5 5 2 3 3 2 5 5 3 3 0 5 6-109 320 5 5 5 5 5 5 5 4 4 0 0 0 1 5 5 2 4 0 4 6-110 320 5 5 5 5 5 5 5 4 0 0 1 3 2 5 5 2 4 0 4 6-111 320 5 5 5 5 5 5 5 2 2 0 1 0 2 5 5 1 4 0 4 6-112 320 5 5 5 5 5 5 5 4 1 0 1 0 1 5 5 3 4 0 4 6-113 320 5 5 5 5 5 5 5 0 0 2 0 0 0 5 5 0 5 0 4 7-001 320 5 3 4 3 3 5 3 0 0 0 1 2 0 0 0 0 7-002 320 5 3 5 4 4 5 3 0 0 0 0 0 0 5 3 0 0 0 0 7-003 320 5 5 5 5 5 5 5 0 0 0 0 0 0 5 5 2 0 0 0 7-004 320 5 4 5 2 5 5 5 0 0 2 0 0 5 5 4 0 0 3 7-005 320 5 4 5 2 2 5 4 0 0 3 1 0 0 4 4 0 0 0 0 7-006 320 5 5 5 3 3 5 4 0 0 3 0 0 0 5 4 0 0 0 3 7-007 320 5 5 5 4 5 5 5 0 0 2 0 0 5 5 0 2 0 0 7-008 320 5 5 5 5 5 5 5 1 0 2 1 3 5 0 0 4 0 3 7-010 320 5 5 5 4 5 5 5 3 1 2 0 0 4 5 5 3 5 0 4 7-011 320 4 3 5 3 4 5 3 4 5 3 3 0 1 5 2 0 0 0 4 7-012 320 5 5 5 1 3 5 0 0 0 3 3 2 5 3 2 1 0 3 7-013 320 4 2 1 1 3 3 0 0 5 0 0 0 1 0 0 0 0 1 7-014 320 5 0 5 1 0 5 0 0 0 0 0 0 3 3 0 0 0 1 7-015 320 5 5 5 5 5 5 5 2 0 3 1 4 5 5 0 5 0 5 7-016 320 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7-017 320 5 5 5 0 2 3 3 0 0 0 0 0 5 0 0 0 0 0 7-018 320 5 4 4 0 0 2 2 0 0 0 0 0 0 2 1 0 0 0 0 7-019 320 3 3 4 0 2 3 3 0 0 0 0 0 1 2 0 0 0 2 7-020 320 5 3 4 0 4 4 3 0 0 0 0 0 0 3 0 0 0 0 2 7-022 320 0 0 1 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 7-024 320 0 0 5 2 2 3 1 0 0 0 0 0 0 3 1 0 0 0 2 7-025 320 3 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 7-026 320 0 0 1 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 7-027 320 5 5 5 5 4 5 5 0 0 0 0 0 0 3 5 0 0 0 2 7-029 320 3 3 5 3 0 0 0 0 2 0 1 7-031 320 4 5 5 3 3 5 5 0 0 0 0 0 0 4 1 0 0 0 0 8-001 320 1 1 1 0 0 1 0 0 0 0 0 0 2 0 0 0 0 0 8-002 320 0 0 3 3 4 5 3 0 0 0 0 0 4 0 0 0 0 1 8-003 320 0 0 0 0 0 2 0 0 0 0 0 0 0 0 0 0 0 0 0 9-001 320 4 4 5 5 3 5 3 0 0 0 0 0 3 4 0 0 0 2 9-002 320 5 5 5 5 5 5 5 4 3 0 0 1 5 5 0 3 0 4 9-003 320 5 5 5 4 5 5 5 4 0 3 3 0 4 5 5 4 4 1 4 9-004 320 5 5 5 5 5 5 4 0 1 2 0 5 5 0 3 0 3 9-005 320 4 4 5 5 4 5 5 0 0 0 0 0 0 4 3 0 0 0 3 9-006 320 5 5 5 4 5 5 5 0 0 2 3 0 4 5 5 0 5 0 4 9-007 320 5 5 5 5 5 5 5 0 0 3 3 1 4 5 5 0 4 0 4 9-008 320 5 5 5 4 5 5 5 4 0 3 4 2 4 5 5 3 5 0 4 9-009 320 4 5 5 5 4 5 5 0 0 0 0 0 5 3 0 0 0 3 9-010 320 5 5 5 4 5 5 5 0 3 3 3 3 3 5 3 2 0 0 3 9-011 320 5 5 5 5 5 5 5 2 2 1 0 1 3 5 5 2 5 0 4 9-012 320 5 5 5 5 5 5 5 1 4 2 4 4 3 5 5 1 2 0 3 9-013 320 5 5 5 5 5 5 5 4 0 3 2 4 5 5 0 4 4 4 9-014 320 5 5 5 4 4 4 3 0 0 0 0 0 2 5 5 0 1 0 2 9-015 320 5 5 5 4 5 5 5 0 0 3 3 2 4 5 5 0 3 0 5 9-016 320 5 5 5 5 5 5 5 0 0 2 3 2 1 5 5 3 3 0 3 9-017 320 4 5 5 4 3 5 3 0 0 0 0 0 0 5 5 0 3 0 3 9-018 320 0 3 3 3 1 1 0 0 0 0 1 0 0 3 3 0 0 0 0 9-019 320 4 5 5 4 4 5 1 0 0 0 0 0 0 3 5 0 0 0 1 9-020 320 5 5 5 5 5 5 4 4 5 3 3 3 5 5 1 2 0 4 9-021 320 5 5 5 4 5 5 5 2 2 3 1 4 5 5 1 4 0 4 9-022 320 5 5 5 0 2 2 2 0 0 0 0 0 0 5 2 0 0 0 0 9-023 320 5 5 5 4 5 5 5 0 0 3 3 0 3 5 5 0 1 0 5 9-024 320 5 5 5 5 5 5 5 3 1 4 4 4 4 5 5 0 3 0 4 9-025 320 5 4 1 3 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 9-026 320 5 4 0 3 0 0 0 0 0 0 0 0 0 0 5 0 0 0 0 9-027 320 5 5 5 5 5 5 5 0 0 2 3 3 2 5 5 0 4 0 4 9-028 320 5 5 5 4 5 5 5 1 4 2 3 4 4 5 5 1 4 3 4 9-029 320 3 3 3 5 4 5 4 0 0 0 0 0 0 3 4 0 4 0 4 10-001  320 3 2 4 1 1 3 0 0 0 0 0 0 0 2 1 0 0 0 0 10-002  320 5 5 5 5 4 5 4 0 0 0 0 0 4 5 0 0 0 0 10-003  320 3 5 5 3 3 4 3 0 0 0 0 0 0 4 2 0 0 0 0 10-004  320 5 5 5 5 5 5 5 3 0 0 0 3 5 5 0 4 0 4 11-002  320 4 4 5 5 5 5 5 0 0 0 0 0 0 5 2 1 2 0 4 12-002  320 5 5 5 5 5 5 5 1 0 2 4 4 4 5 5 1 2 3 5 13-001  320 5 5 5 5 5 5 5 1 0 0 0 0 0 5 5 0 5 0 4 13-002  320 5 5 5 5 5 5 5 2 0 5 3 4 4 5 5 2 5 3 4 13-003  320 5 5 5 5 5 5 5 4 0 0 1 3 1 5 5 3 5 0 4 13-004  320 5 5 5 5 5 5 5 1 0 4 2 4 3 5 5 1 5 0 4 13-005  320 5 5 5 5 5 5 5 0 0 0 0 0 0 5 4 0 5 0 3 13-006  320 5 5 5 5 5 5 5 4 3 2 3 2 5 5 2 5 3 4 14-001  320 5 5 5 5 5 5 5 4 0 0 0 0 2 5 5 2 4 0 4 14-002  320 5 5 5 5 5 5 5 4 0 0 0 0 0 4 5 1 3 0 4

INDUSTRIAL APPLICABILITY

The ketone or oxime compound of the present invention is a novel compound and is useful as herbicides for rice, corn, soybean, wheat, beet, and rapeseed. 

1. A ketone or oxime compound or a salt thereof of Formula (1):

[wherein B is a ring of any one of B-1, B-2, or B-3;

Q is an oxygen atom, a sulfur atom, or NOR⁷; A is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁵, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, —S(O)_(r2)R¹, —C(O)OR¹, —C(S)OR¹, —C(O)SR¹, —C(S)SR¹, —C(O)R², —C(S)R², —C(O)N(R⁴)R³, —C(S)N(R⁴)R³, —S(O)₂N(R⁴)R³, —P(O)(OR¹)₂, or —P(S)(OR¹)₂; R¹ is C₁₋₈ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, phenyl, or phenyl substituted with (Z²)_(q2); R² is a hydrogen atom, C₁₋₈ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, —C(═NOR³¹)R³², phenyl, phenyl substituted with (Z²)_(q2), naphthyl, naphthyl substituted with (Z²)_(q2), D1-1 to D1-42, D1-81, or D1-84; R³ and R⁴ are each independently a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, phenyl, phenyl substituted with (Z²)_(q2), D1-32, D1-33 or D1-34, or R³ optionally forms a 3- to 8-membered ring together with a nitrogen atom to which R³ and R⁴ are bonded by forming a C₂₋₇ alkylene chain or a C₂₋₇ alkenylene chain together with R⁴, and at this time, the alkylene chain or the alkenylene chain optionally contains one oxygen atom, sulfur atom, or nitrogen atom and optionally substituted with C₁₋₆ alkyl, oxo, or thioxo; R⁵ is a halogen atom, cyano, nitro, C₃₋₈ cycloalkyl, —OR³¹, —S(O)_(r2)R³¹, —C(O)OR³¹, —C(O)R³², —N(R³⁴)R³³, —Si(R^(32a))(R^(32b))R^(32c), phenyl, phenyl substituted with (Z²)_(q2), D1-1, D1-32, D1-33, or D1-34, or when two R⁵s are substituents on a same carbon, the two R⁵s optionally form oxo, thioxo, imino, C₁₋₆ alkylimino, C₁₋₆ alkoxyimino, or C₁₋₆ alkylidene, together with each other; R⁶ is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R¹⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R¹⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R¹⁵, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R¹⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R¹⁵, —C(═NOR¹⁶)R¹⁷, phenyl, phenyl substituted with (Z¹)_(q1), D1-32, D1-33, D1-34, D1-36, D1-37, or D1-38; R⁷ is a hydrogen atom, C₁₋₈ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R^(15b), C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R^(15b), C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R^(15b), C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R^(15b), C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R^(15b), phenyl, or phenyl substituted with (Z¹)_(q1); R^(8a), R^(8b), R^(9a), and R^(9b) are each independently a hydrogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, —OR^(16a), —S(O)_(r1)R^(16a), —C(O)OR^(16a), —C(O)R^(17a), —C(O)N(R^(19a))R^(18a), —C(═NOR^(16a))R^(17a), phenyl, or phenyl substituted with (Z¹)_(q1); R¹⁰, R¹¹ and R¹² are each independently a hydrogen atom or C₁₋₆ alkyl; R¹⁵ is a halogen atom, cyano, C₃₋₈ cycloalkyl, —OR¹⁶, —S(O)_(r1)R¹⁶, phenyl, phenyl substituted with (Z¹)_(q1), D1-7, D1-11, D1-22, D1-32, D1-33, or D1-34; R^(15b) is a halogen atom, cyano, C₃₋₈ cycloalkyl, halo (C₃₋₈) cycloalkyl, —OR^(16b), —S(O)_(r1)R^(16b), —C(O)OR^(16b), —C(O)N(R^(18b))R^(19b), —C(═NOR^(16b))R^(17b), —N(R^(18b))R^(19b), —Si(R^(32a))(R^(32b))R^(32c), phenyl, phenyl substituted with (Z¹)_(q1), D1-32, D1-33, D1-34, D1-36, D1-37, D1-38, D1-81, or D1-84, or when two R^(15b)s are substituents on a same carbon, the two R^(15b)s optionally form oxo, thioxo, imino, C₁₋₆ alkylimino, C₁₋₆ alkoxyimino, or C₁₋₆ alkylidene, together with each other; R¹⁶, R^(16a), R^(16b), R¹⁷, R^(17a), R^(17b), R^(18a), and R^(19a) are each independently a hydrogen atom or C₁₋₆ alkyl; R^(18b) and R^(19b) are each independently a hydrogen atom, C₁₋₆ alkyl, or (C₁₋₆) alkyl arbitrarily substituted with R²⁰, or R^(18b) optionally forms a 3- to 8-membered ring together with a nitrogen atom to which R^(18b) and R^(19b) are bonded by forming a C₂₋₇ alkylene chain or a C₂₋₇ alkenylene chain together with R^(19b), and at this time, the alkylene chain or the alkenylene chain optionally contains one oxygen atom, sulfur atom, or nitrogen atom and optionally substituted with oxo or thioxo; R²⁰ is phenyl or phenyl substituted with (Z¹)_(q1); D1-1 to D1-42, D1-81, and D1-84 each are a ring of the following structure;

X¹ is a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, or C₃₋₈ cycloalkyl, when g2, g3, or g4 is an integer of 2 or larger, each X¹ is the same as or different from each other, and further when two X's are adjacent, the two adjacent X's optionally form a 6-membered ring together with carbon atoms to which each X¹ is bonded by forming —CH═CHCH═CH—, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is optionally substituted with a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, or C₁₋₆ alkylsulfonyl; X^(1a) is a hydrogen atom or C₁₋₆ alkyl; X^(1b) is C₁₋₆ alkyl; Z is a halogen atom, cyano, nitro, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁴⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁴⁵, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁴⁵, —OR⁴¹, —S(O)_(r3)R⁴¹, —C(O)OR⁴¹, —C(O)R⁴², —C(═NOR⁴¹)R⁴², —N(R⁴⁴)R⁴³, phenyl, phenyl substituted with (Z³)_(q3), D1-1, D1-2, D1-7, D1-10, D1-11, D1-22, D1-32, D1-33, D1-34, D1-36, D1-37, or D1-38, and when q is an integer of 2 or larger, each Z is the same as or different from each other; Z¹ is a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, or C₁₋₆ alkoxycarbonyl, and when q1 is an integer of 2 or larger, each Z¹ is the same as or different from each other, Z² is a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, —OR⁵¹, —S(O)_(r2)R⁵¹, —C(O)OR^(51a), —C(O)R⁵², —C(O)N(R⁵⁴)R⁵³, —C(S)N(R⁵⁴)R⁵³, or —N(R⁵⁴)R⁵³, when q2 is an integer of 2 or larger, each Z² is the same as or different from each other, and further when two Z²s are adjacent, the two adjacent Z²s optionally form a 6-membered ring together with carbon atoms to which each Z² is bonded by forming —N═CHCH═CH—, —CH═NCH═CH—, —N═NCH═CH—, —CH═NN═CH—, —N═CHCH═N—, or —N═CHN═CH—, and at this time, the hydrogen atom bonded to each carbon atom forming the ring is optionally substituted with a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, or C₁₋₆ alkylsulfonyl; Z³ is a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, halo (C₁₋₆) alkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, or C₁₋₆ alkylsulfonyl, and when q3 is an integer of 2 or larger, each Z³ is the same as or different from each other; R³¹ is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R³⁵, —C(O)R³⁷, phenyl, phenyl substituted with (Z²)_(q2), naphthyl, or naphthyl substituted with (Z²)_(q2); R³² is a hydrogen atom, C₁₋₆ alkyl, or (C₁₋₆) alkyl arbitrarily substituted with R³⁵; R^(32a), R^(32b), and R^(32c) are each independently C₁₋₆ alkyl; R³³ and R³⁴ are each independently a hydrogen atom, C₁₋₆ alkyl, —C(O)OR³⁶, or —C(O)R³⁷; R³⁵ is a halogen atom, C₁₋₆ alkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, or phenyl; R³⁶ is C₁₋₆ alkyl; R³⁷ is a hydrogen atom, C₁₋₆ alkyl, phenyl, or phenyl substituted with (Z²)_(q2); R⁴¹ is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁴⁵, phenyl, phenyl substituted with (Z³)_(q3), D1-32, D1-33, or D1-34; R⁴² is a hydrogen atom or C₁₋₆ alkyl; R⁴³ and R⁴⁴ are each independently a hydrogen atom, C₁₋₆ alkyl, C₁₋₆ alkoxycarbonyl, or C₁₋₆ alkylcarbonyl; R⁴⁵ is a halogen atom, C₃₋₈ cycloalkyl, —OH, C₁₋₆ alkoxy, C₁₋₁₀ alkoxycarbonyl, —Si(R^(32a))(R^(32b))R^(32c), phenyl, phenyl substituted with (Z³)_(q3), D1-32, D1-33, or D1-34, or when two R⁴⁵s are substituents on a same carbon, the two R⁴⁵s optionally form oxo, thioxo, imino, C₁₋₆ alkylimino, C₁₋₆ alkoxyimino, or C₁₋₆ alkylidene, together with each other; R⁵¹ is a hydrogen atom, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, phenyl, phenyl arbitrarily substituted with a halogen atom, or D1-39; R^(51a) and R⁵² are each independently a hydrogen atom or C₁₋₆ alkyl; R⁵³ and R⁵⁴ are each independently a hydrogen atom, C₁₋₆ alkyl, or C₁₋₆ alkylcarbonyl; f5 is an integer of 0, 1, 2, 3, 4, or 5; f7 is an integer of 0, 1, 2, 3, 4, 5, 6, or 7; g1 and p are each independently an integer of 0 or 1; g2, m, n, r1, r2, and r3 are each independently an integer of 0, 1, or 2; g3 is an integer of 0, 1, 2, or 3; g4 is an integer of 0, 1, 2, 3, or 4; and q, q1, q2, and q3 are each independently an integer of 1, 2, 3, 4, or 5].
 2. The ketone or oxime compound or a salt thereof according to claim 1, wherein B is a ring of either B-1-a or B-2-a; and

Z^(a), Z^(c) and Z^(e) are each independently a hydrogen atom, a halogen atom, cyano, nitro, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁴⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁴⁵, —OR⁴¹, —S(O)_(r3)R⁴¹, —C(O)OR⁴¹, —C(O)R⁴², —C(═NOR⁴¹)R⁴², —N(R⁴⁴)R⁴³, phenyl, phenyl substituted with (Z³)_(q3), D1-1, D1-2, D1-7, D1-10, D1-11, D1-22, D1-32, D1-33, D1-34, D1-36, D1-37, or D1-38.
 3. The ketone compound or the salt thereof according to claim 2, wherein Q is an oxygen atom.
 4. The oxime compound or a salt thereof according to claim 2, wherein Q is ═NOR⁷.
 5. The ketone compound or the salt thereof according to claim 3, wherein A is a hydrogen atom, C₁₋₆ alkyl, or —C(O)R²; R² is C_(1-s) alkyl; R⁶ is C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R¹⁵, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, —C(═NOR¹⁶)R¹⁷, phenyl, phenyl substituted with (Z¹)_(q1), or D1-32; R^(8a) is a hydrogen atom, C₁₋₆ alkyl, —C(O)OR^(16a), or —C(O)R^(17a); R^(9a) is a hydrogen atom or C₁₋₆ alkyl; R^(8b) and R^(9b) are hydrogen atoms; R¹⁰, R¹¹, and R¹² are hydrogen atoms; R¹⁵ is a halogen atom, C₃₋₈ cycloalkyl, —OR¹⁶, or phenyl; R¹⁶, R^(16a), R¹⁷, and R^(17a) are each independently C₁₋₆ alkyl; X¹ is halo (C₁₋₆) alkyl; Z^(a), Z^(c) and Z^(e) are each independently a hydrogen atom, a halogen atom, C₁₋₆ alkyl, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkynyl, —OR⁴¹, phenyl, phenyl substituted with (Z³)_(q3), D1-7, D1-11, D1-22, D1-32, or D1-37; Z¹ is a halogen atom; Z³ is a halogen atom, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, halo (C₁₋₆) alkoxy, or C₁₋₆ alkylthio; R⁴¹ is C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁴⁵, phenyl, D1-32, or D1-34; R⁴⁵ is a halogen atom, phenyl, or D1-34; g2, g3, and p are 0; q1 and q3 are integers of 1; and g4, m, and n are each independently an integer of 0 or
 1. 6. The ketone compound or the salt thereof according to claim 5, wherein B is B-1-a; Z^(a) is a halogen atom, C₁₋₆ alkyl, or C₁₋₆ alkoxy; Z^(c) is a halogen atom, C₁₋₆ alkyl, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkynyl, —OR⁴¹, phenyl, phenyl substituted with (Z³)_(q3), D1-7, D1-11, D1-22, D1-32, or D1-37; and Z^(e) is a halogen atom or C₁₋₆ alkyl.
 7. The oxime compound or the salt thereof according to claim 4, wherein A is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, —S(O)_(r2)R¹, —C(O)OR¹, —C(O)SR¹, —C(S)OR¹, —C(O)R², —C(O)N(R⁴)R³, —C(S)N(R⁴)R³, or —S(O)₂N(R⁴)R³; R¹ is C₁₋₈ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, phenyl, or phenyl substituted with (Z²)_(q2); R² is C₁₋₈ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkyl, (C₃₋₈) cycloalkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁵, C₃₋₈ cycloalkenyl, (C₃₋₈) cycloalkenyl arbitrarily substituted with R⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁵, —C(═NOR³¹)R³², phenyl, phenyl substituted with (Z²)_(q2), D1-5, D1-6, D1-8, D1-10, or D1-81; R³ is C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁵, C₂₋₆ alkenyl, phenyl, or phenyl substituted with (Z²)_(q2), or R³ forms a 5- to 6-membered ring together with a nitrogen atom to which R³ and R⁴ are bonded by forming a C₄ or C₅ alkylene chain together with R⁴, and at this time, the alkylene chain optionally contains one oxygen atom or nitrogen atom and is optionally substituted with C₁₋₆ alkyl; R⁴ is C₁₋₆ alkyl, C₂₋₆ alkenyl, or phenyl; R⁵ is a halogen atom, cyano, C₃₋₈ cycloalkyl, —OR³¹, —S(O)_(r2)R³¹, —C(O)OR³¹, —C(O)R³², —N(R³⁴)R³³, —Si(R^(32a))(R^(32b))R^(32c), phenyl, phenyl substituted with (Z²)_(q2), or D1-1, or when two R⁵s are substituents on a same carbon, the two R⁵s optionally form C₁₋₆ alkoxyimino together with each other; R⁶ is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R¹⁵, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, —C(═NOR¹⁶)R¹⁷, phenyl, phenyl substituted with (Z¹)_(q1) or, D1-32; R⁷ is a hydrogen atom, C₁₋₇ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R^(15b), C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, C₃₋₈ cycloalkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R^(15b), C₂₋₆ alkynyl, or phenyl; R^(8a) is a hydrogen atom, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, —C(O)OR^(16a), —C(═NOR^(16a))R^(17a), or phenyl substituted with (Z¹)_(q1); R^(9a) is a hydrogen atom or C₁₋₆ alkyl; R^(8b) and R^(9b) are hydrogen atoms; R¹² is a hydrogen atom; R¹⁵ is a halogen atom, C₃₋₈ cycloalkyl, or —OR¹⁶; R^(15b) is a halogen atom, cyano, C₃₋₈ cycloalkyl, halo (C₃₋₈) cycloalkyl, —OR^(16b), —S(O)_(r1)R^(16b), —C(O)OR^(16b), —C(O)N(R^(18b))R^(19b), —C(═NOR^(16b))R^(17b), —N(R^(18b))R^(19b), —Si(R^(32a))(R^(32b))R^(32c), phenyl, phenyl substituted with (Z¹)_(q1), D1-32, or D1-84; R¹⁶, R^(16a), R¹⁷, R^(17a), and R^(17b) are each independently C₁₋₆ alkyl; R^(18b) is a hydrogen atom, C₁₋₆ alkyl, or (C₁₋₆) alkyl arbitrarily substituted with R²⁰, or R^(18b) forms a 6-membered ring together with a nitrogen atom to which R^(18b) and R^(19b) are bonded by forming a C₅ alkylene chain together with R^(19b), and at this time, the alkylene chain contains one oxygen atom; R^(19b) is a hydrogen atom or C₁₋₆ alkyl; R²⁰ is phenyl substituted with (Z¹)_(q1); X¹ is a halogen atom, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, or C₃₋₈ cycloalkyl, g3 is an integer of 2, and further the two adjacent X¹s form a 6-membered ring together with carbon atoms to which each X¹ is bonded by forming —CH—CHCH—CH—, and at this time, one hydrogen atom bonded to each carbon atom forming the ring is arbitrarily substituted with a halogen atom; X^(1a) is C₁₋₆ alkyl; Z^(a), Z^(c), and Z^(e) are each independently a hydrogen atom, a halogen atom, cyano, nitro, C₁₋₆ alkyl, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁴⁵, —OR⁴¹, —S(O)_(r3)R⁴¹, —C(O)OR⁴¹, —C(O)R⁴², —C(═NOR⁴¹)R⁴², —N(R⁴⁴)R⁴³, phenyl, phenyl substituted with (Z³)_(q3), D1-2, D1-7, D1-11, D1-22, D1-32, D1-33, D1-34, or D1-37, Z¹ is a halogen atom, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, or C₁₋₆ alkoxycarbonyl, and when q1 is an integer of 2 or larger, each Z¹ is the same as or different from each other; Z² is a halogen atom, cyano, nitro, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, —OR⁵¹, —S(O)_(r2)R⁵¹, —C(O)OR^(51a), —C(O)R⁵², or —C(O)N(R⁵⁴)R⁵³, when q2 is an integer of 2 or larger, each Z² is the same as or different from each other, and further when the two Z²s are adjacent, the two adjacent Z²s optionally form a 6-membered ring together with carbon atoms to which each Z² is bonded by forming —N═CHCH—CH—, and at this time, one hydrogen atom bonded to each carbon atom forming the ring is arbitrarily substituted with a halogen atom; Z³ is a halogen atom, C₁₋₆ alkyl, halo (C₁₋₆) alkyl, C₁₋₆ alkoxy, halo (C₁₋₆) alkoxy, or C₁₋₆ alkylthio, and when q3 is an integer of 2 or larger, each Z³ is the same as or different from each other; R³¹ is C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R³⁵, —C(O)R³⁷, phenyl, phenyl substituted with (Z²)_(q2), or naphthyl; R³² is C₁₋₆ alkyl or (C₁₋₆) alkyl arbitrarily substituted with R³⁵; R³³ is —C(O)R³⁷; R³⁴ is C₁₋₆ alkyl; R³⁵ is a halogen atom, C₁₋₆ alkylthio, or phenyl; R³⁷ is C₁₋₆ alkyl or phenyl; R⁴¹ is a hydrogen atom, C₁₋₆ alkyl, (C₁₋₆) alkyl arbitrarily substituted with R⁴⁵, phenyl, or D1-32; R⁴² is C₁₋₆ alkyl; R⁴³ is C₁₋₆ alkoxycarbonyl; R⁴⁴ is a hydrogen atom; R⁴⁵ is a halogen atom, C₃₋₈ cycloalkyl, —OH, C₁₋₆ alkoxy, C₁₋₁₀ alkoxycarbonyl, —Si(R^(32a))(R^(32b))R^(32c), phenyl, or D1-34; R⁵¹ is C₁₋₆ alkyl, halo (C₁₋₆) alkyl, phenyl arbitrarily substituted with a halogen atom, or D1-39; R^(51a) is C₁₋₆ alkyl; R⁵³ and R⁵⁴ are each independently C₁₋₆ alkyl; g2 is an integer of 0, 1, or 2; g3 and r1 are each independently an integer of 0, 1, or 2; g4, m, and n are each independently an integer of 0 or 1; f7, p, and r3 are 0; q is an integer of 2 or 3; q1 is an integer of 1 or 2; q2 is an integer of 1, 2, or 3; q3 is an integer of 1, 2, or 3; and r2 is an integer of 0 or
 2. 8. The oxime compound or the salt according to claim 7, wherein B is B-1-a; Z^(a) is a halogen atom, C₁₋₆ alkyl, C₁₋₆ alkoxy, or C₁₋₆ alkylthio; Z^(c) is a hydrogen atom, a halogen atom, cyano, nitro, C₁₋₆ alkyl, C₃₋₈ cycloalkyl, C₂₋₆ alkenyl, (C₂₋₆) alkenyl arbitrarily substituted with R⁴⁵, C₂₋₆ alkynyl, (C₂₋₆) alkynyl arbitrarily substituted with R⁴⁵, —OR⁴¹, —S(O)_(r3)R⁴¹, —C(O)OR⁴¹, —C(O)R⁴², —C(═NOR⁴¹)R⁴², —N(R⁴⁴)R⁴³, phenyl, phenyl substituted with (Z³)_(q3), D1-2, D1-7, D1-11, D1-22, D1-32, D1-33, D1-34, or D1-37; Z^(e) is a halogen atom, C₁₋₆ alkyl, or C₁₋₆ alkoxy; X¹ is a halogen atom or halo (C₁₋₆) alkyl; and g3 is an integer of 0 or
 1. 9. An agricultural chemical comprising: one or more of compounds selected from the ketone or oxime compound or the salt thereof as claimed in claim 1 as an active component.
 10. A herbicide comprising: one or more of compounds selected from the ketone or oxime compound or the salt thereof as claimed in claim 1 as an active component. 